Reaction_05_24_2011_125932

Task HistoryMay 24, 2011 2:45 PMExplore reactions by structure variable only at specified positions structure initiated Query

Explore completeExplore resultsAnswer set 11 created with 65 reactions

SciFinder® Page 1

1. Single Step

90%

Overview

Steps/Stages Notes

1.1 R:PPh3, S:MeCN, 15 min, rt1.2 R: 1 h, 40°C

Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2

ReferencesSynthesis of benzyl bromides withhexabromoacetone: an alternative path todrug intermediatesBy Joseph, Kara M., Larraza-Sanchez, IsabelFrom Tetrahedron Letters, 52(1), 13-16; 2011

CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.2. Single Step

100%

Overview

Steps/Stages Notes

1.1 R:PPh3, S:MeCN, 15 min, rt1.2 R: overnight, rt

1) optimization study (optimized on solventand temperature), Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 2, Most stagesin any one step: 2

ReferencesSynthesis of benzyl bromides withhexabromoacetone: an alternative path todrug intermediatesBy Joseph, Kara M., Larraza-Sanchez, IsabelFrom Tetrahedron Letters, 52(1), 13-16; 2011


SciFinder® Page 2

75%

Overview

Steps/Stages Notes

1.1 R:PBr3, S:THF, 5 min, rt 1) alternative reaction conditions shown,polyimide film microreactor used, Reactants: 1,Reagents: 1, Solvents: 1, Steps: 1, Stages: 1,Most stages in any one step: 1

ReferencesMonolithic and Flexible Polyimide FilmMicroreactors for Organic MicrochemicalApplications Fabricated by Laser AblationBy Min, Kyoung-Ik et alFrom Angewandte Chemie, InternationalEdition, 49(39), 7063-7067, S7063/1-S7063/3; 2010


76%

Overview

Steps/Stages Notes

1.1 R:Br2, R:PPh3, S:CH2Cl2, 0°C; 30 min, 0°C

1.2 3 h, 0°C


ReferencesIdentification and biosynthesis of troponederivatives and sulfur volatiles produced bybacteria of the marine Roseobacter cladeBy Thiel, Verena et alFrom Organic & Biomolecular Chemistry,8(1), 234-246; 2010

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94%

Overview

Steps/Stages Notes

1.1 R:KBr, C:H2SO4, S:H2O, 20 min, heated; 4 h, reflux 1) optimization study, optimized onstoichiometry, catalyst and solvent amount,time, Reactants: 1, Reagents: 1, Catalysts: 1,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesSynthesis of benzyl bromide using potassiumbromide and concentrated sulfuric acidmethodBy Song, Zhiguo et alFrom Gongye Cuihua, 16(1), 48-50; 2008


94%

Overview

Steps/Stages Notes

1.1 R:H2SO4, R:KBr, S:H2O, 20 min, reflux; 4 h, reflux Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesClean synthesis and characterization ofbromoalkanesBy Song, Zhiguo et alFrom Jingxi Huagong Zhongjianti, 38(1), 37-39; 2008

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86%

Overview

Steps/Stages Notes

1.1 R:Br2, R:PPh3, R:1H-Imidazole, S:CH2Cl2, 0°C; 0°C → 22°C Reactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesN-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide as a New Scaffold thatProvides Rapid Access to AntimicrotubuleAgents: Synthesis and Evaluation ofAntiproliferative Activity Against SelectCancer Cell LinesBy Stefely, Jonathan A. et alFrom Journal of Medicinal Chemistry, 53(8),3389-3395; 2010

Experimental Procedure9a, yield 86%


80%

Overview

Steps/Stages Notes

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1.1 R:PBr3, S:CH2Cl2, 1 h, 0°C; 15 h, 20°C Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesCollision-induced loss of AgH from Ag+adducts of alkylamines, aminocarboxylicacids and alkyl benzyl ethers leadsexclusively to thermodynamically favoredproduct ionsBy Schaefer, Mathias et alFrom Journal of Mass Spectrometry, 44(2),278-284; 2009


polymer-supported polymer-supported93%

Overview

Steps/Stages Notes

1.1 R:PBr3, S:CH2Cl2, 0°C → rt Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesA Yb(OTf)3/PEG-supported quaternaryammonium salt catalyst system for a three-component Mannich-type reaction in aqueousmediaBy Hong, Deng et alFrom Synlett, (7), 1107-1110; 2009


98%

Overview

Steps/Stages Notes

SciFinder® Page 6

1.1 R:Cyanurictrichloride, S:DMF, 25°C

1.2 R:NaBr, S:CH2Cl2, 10 h, 25°C

1.3 15 min, rt


ReferencesA chemoselective, easy bromination of(hydroxymethyl)phenolsBy Nieddu, Giammario et alFrom Synthesis, (24), 3937-3940; 2008


60%

Overview

Steps/Stages Notes

1.1 R:LiBr, R:PPh3, R:EtO2CN=NCO2Et, R:N2(CO2CHMe2)2, S:THF 1) PPh3, DEAD or DIAD, LiBr, THF, 0 C,Bromination, Halogenation, Substitution,Reactants: 1, Reagents: 4, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesThe Mitsunobu reactionBy Hughes, David L.From Organic Reactions (Hoboken, NJ,United States), 42(), No pp. given; 1992


91%

Overview

Steps/Stages Notes

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1.1 R:

R:PPh3,R:EtO2CN=NCO2Et,R:N2(CO2CHMe2)2,

S:THF 1) PPh3, DEAD or DIAD, MeBr/MTD, THF,r.t./6 h., Bromination, Halogenation,Substitution, Reactants: 2, Reagents: 4,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesThe Mitsunobu reactionBy Hughes, David L.From Organic Reactions (Hoboken, NJ,United States), 42(), No pp. given; 1992


76%

Overview

Steps/Stages Notes

1.1 R:Ph3PBr2, S:CCl41) Ph3PBr2, CCl4, 80 C/20 min., Bromination,Halogenation, Substitution, Reactants: 1,Reagents: 1, Solvents: 1, Steps: 1, Stages: 1,Most stages in any one step: 1

ReferencesReplacement of alcoholic hydroxyl groups byhalogens and other nucleophiles viaoxyphosphonium intermediatesBy Castro, Bertrand R.From Organic Reactions (Hoboken, NJ,United States), 29(), No pp. given; 1983


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Overview

Steps/Stages Notes

1.1 C:Et3SiH, C:PdCl2, C:CH2Br21) Additional Ionic Hydrogenation andReductive Substitutions, Reactants: 1,Catalysts: 3, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesTriethylsilaneBy Fry, James L. et alFrom e-EROS Encyclopedia of Reagents forOrganic Synthesis, (), No pp. given; 2001


98%

Overview

Steps/Stages Notes

1.1 R:

R:PPh3,

S:CH2Cl2, 15 min, rt Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesHexabromoacetone and ethyltribromoacetate: a highly efficient reagent forbromination of alcoholBy Tongkate, Pratoomrat et alFrom Tetrahedron Letters, 49(7), 1146-1148;2008


92%

SciFinder® Page 9

Overview

Steps/Stages Notes

1.1 R:HBr, S:PhCH2OH, 4 h, reflux Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesSimple synthesis of fresh alkyl iodides usingalcohols and hydriodic acidBy Klein, Suzane M. et alFrom Tetrahedron Letters, 49(16), 2638-2641; 2008


80%

Overview

Steps/Stages Notes

1.1 R:Br2, R:PPh3, S:MeCN, 2 h, 55°C Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesAn unprecedented rearrangement in collision-induced mass spectrometric fragmentation ofprotonated benzylaminesBy Bialecki, Jason et alFrom Journal of Mass Spectrometry, 41(9),1195-1204; 2006


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80%

Overview

Steps/Stages Notes




80%

Overview

Steps/Stages Notes




SciFinder® Page 11

70%

Overview

Steps/Stages Notes

1.1 S:CH2Cl2, rt → -40°C

1.2 R:BBr3, 15 min, -40°C; 30 min, 0°C


ReferencesMaking a Difference on Excited-StateChemistry by Controlling Free Space within aNanocapsule: Photochemistry of 1-(4-Alkylphenyl)-3-phenylpropan-2-onesBy Sundaresan, Arun Kumar, Ramamurthy,V.From Organic Letters, 9(18), 3575-3578;2007

Experimental Procedure2. 1-(Bromomethyl)-4-alkylbenzene (9): To a solution of 8 (1 equivalent) in dichloromethane cooled to -40 °C in a dry ice /acetone bath under nitrogen atmosphere, boron tribromide (1.1 equivalents) wasadded over 15 min and was stirred for 30 min period at 0 °C. The solvent was distilled and the residuewas passed through a silica column eluting with hexane to obtain 9 (colorless liquid). yield 70%. 99 %pure by GC.


90%

Overview

Steps/Stages Notes

1.1 R:CBr4, R:PPh3, S:CH2Cl2Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesDesign and synthesis of phenethylbenzo[1,4]oxazine-3-ones as potent inhibitorsof PI3KinaseγBy Lanni, Thomas B. et alFrom Bioorganic & Medicinal ChemistryLetters, 17(3), 756-760; 2007

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95%

Overview

Steps/Stages Notes

1.1 R:

R:Br2,

S:CH2Cl2, rt

1.2 R:Na2S2O3, rt

1) NBS can be used instead of Br2, alternativereaction conditions shown, Reactants: 1,Reagents: 3, Solvents: 1, Steps: 1, Stages: 2,Most stages in any one step: 2

References4-Aminophenyldiphenylphosphinite (APDPP),a new heterogeneous and acid scavengerphosphinite - Conversion of alcohols,trimethylsilyl, and tetrahydropyranyl ethers toalkyl halides with halogens or N-halosuccinimidesBy Firouzabadi, Habib et alFrom Canadian Journal of Chemistry, 84(7),1006-1012; 2006


100%

Overview

Steps/Stages Notes

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1.1 R:Br2, S:908227-64-5, rt1.2 R: 0.5 h, 80°C; 80°C → rt


ReferencesA new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highlyselective bromination, thiocyanation, orisothiocyanation of alcohols and trimethylsilyland tetrahydropyranyl ethersBy Iranpoor, Nasser et alFrom Tetrahedron Letters, 47(31), 5531-5534; 2006


100%

Overview

Steps/Stages Notes

1.1 R:Br2, S:908227-64-5, rt1.2 R: 1 h, 80°C; 80°C → rt




100%

Overview

SciFinder® Page 14

Steps/Stages Notes

1.1 R:Br2, S:908227-64-5, rt1.2 R: 80°C; 80°C → rt




100%

Overview

Steps/Stages Notes

1.1 R:Br2, S:908227-64-5, rt1.2 R: 80°C; 80°C → rt




95%

SciFinder® Page 15

Overview

Steps/Stages Notes

1.1 R:Br2, S:908227-64-5, rt

1.2 80°C; 80°C → rt




90%

Overview

Steps/Stages Notes

1.1 R:

R:PPh3,

S:CH2Cl2, rt Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesFacile conversion of alcohols into theirbromides and iodides by N-bromo- and N-iodosaccharins/triphenylphosphine underneutral conditionsBy Firouzabadi, Habib et alFrom Tetrahedron Letters, 47(11), 1771-1775; 2006


89%

SciFinder® Page 16

Overview

Steps/Stages Notes

1.1 R:PBr3 R: rt

1.2 S:CHCl3, rt

1.3 R:K2CO3, S:H2O, 24 h, rt

1) in the dark, quadraphasic phase-vanishingmethod used, Reactants: 1, Reagents: 3,Solvents: 2, Steps: 1, Stages: 3, Most stagesin any one step: 3

ReferencesQuadraphasic phase-vanishing method.Application to bromination reactions thatproduce acidic by-productsBy Rahman, Md. Taifur et alFrom Synlett, (17), 2664-2666; 2005


97%

Overview

Steps/Stages Notes

1.1 R:PCl3 (react with silica gel to obtain silphos), rt; 30 min, rt

1.2 R:Br2, S:MeCN, rt; rt → reflux; 5 min, reflux

1) in-situ generated agent, silica gel used inthe first stage, Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 2, Most stagesin any one step: 2

ReferencesSilicaphosphine (Silphos): a filterable reagentfor the conversion of alcohols and thiols toalkyl bromides and iodidesBy Iranpoor, Nasser et alFrom Tetrahedron, 61(23), 5699-5704; 2005


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100%

Overview

Steps/Stages Notes



1) in-situ generated agent, optimization study,optimized on molar ratio of bromine andsilicagel, silica gel used in the first stage,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 2, Most stages in any one step: 2



100%

Overview

Steps/Stages Notes



1) in-situ generated agent, optimization study,optimized on temperature of the first stage,silica gel used in the first stage, Reactants: 1,Reagents: 2, Solvents: 1, Steps: 1, Stages: 2,Most stages in any one step: 2


CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.

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33. Single Step

100%

Overview

Steps/Stages Notes

1.1 R:P(OEt)3, rt; rt → 110°C; 144 h, 110°C

1.2 R:Br2, S:MeCN, rt; rt → reflux; 0.33 h, reflux

1) in-situ generated agent, optimization study,optimized on supporting bed,molar ratio ofreagents,reaction time, silica gel used in firststage, Reactants: 1, Reagents: 2, Solvents: 1,Steps: 1, Stages: 2, Most stages in any onestep: 2



99%

Overview

Steps/Stages Notes

1.1 R:SOCl2, C:1H-Benzotriazole, S:CH2Cl2, 5 min

1.2 R:KBr, S:DMF, 30 min

Reactants: 1, Reagents: 2, Catalysts: 1,Solvents: 2, Steps: 1, Stages: 2, Most stagesin any one step: 2

ReferencesEfficient and selective halogenation of allylicand benzylic alcohols under mild conditionsBy Bandgar, Babasaheb P., Bettigeri,Sampada V.From Monatshefte fuer Chemie, 135(10),1251-1255; 2004

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93%

Overview

Steps/Stages Notes

1.1 R:t-BuBr R:

,

S:343851-31-0, 0.8 h 1) green chemistry-reagent, ultrasound, ionicliquid may be recycled, alternate preparationsdescribed, Reactants: 1, Reagents: 2,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesDirect halogenation of alcohols and theirderivatives with tert-Butyl halides in the ionicliquid [pmIm]Br under sonication conditions -a novel, efficient and green methodologyBy Ranu, Brindaban C., Jana, RanjanFrom European Journal of OrganicChemistry, (4), 755-758; 2005


98%

Overview

Steps/Stages Notes

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1.1 C:85100-78-3, S:85100-78-3, 15 h, 90°C Reactants: 1, Catalysts: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesMethod for converting primary alcohol orcyclohexanol into alkyl halide in acidic ionliquid [Hmin]+X- (X = Cl, Br, I)By Tang, Jie et alFrom Faming Zhuanli Shenqing GongkaiShuomingshu, 1440958, 10 Sep 2003


99%

Overview

Steps/Stages Notes

1.1 R:

,

S:101023-58-9, 12 h, 120°C 1) Other product also detected, The reagentitself acts as catalyst which can be recycledand reused, Green chemistry-catalyst, reagentand solvent, Reactants: 1, Reagents: 1,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesImmobilization of HX. [Hmim]X ashalogenating agent, recyclable catalyst, andmedium for conversion of alcohols to alkylhalidesBy Wu, Hai-Hong et alFrom Chinese Journal of Chemistry, 22(7),619-621; 2004

CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.38. 2 Steps

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Overview

Steps/Stages Notes

1.1 R:MeSO3H, S:THF, 2 d, 25°C

1.2 R:NaOBr, R:LiBr, S:H2O, S:EtCH2Et, S:DMSO, rt; 30 min, < 20°C

2.1 S:CDCl3, 1 h, rt

2) photochemical, addition of H-donorschanges product distribution, Reactants: 2,Reagents: 3, Solvents: 5, Steps: 2, Stages: 3,Most stages in any one step: 2

ReferencesArylmethyl radicals fromarylmethoxybromodiazirinesBy Moss, Robert A., Fu, XiaolinFrom Organic Letters, 6(19), 3353-3356;2004

Experimental ProcedureStep 1General/Typical Procedure: A mixture of 2-naphthylmethanol (10.0 g, 63.2 mmol), cyanamide (2.66g,63.2 mmol), methanesulfonic acid (4.10 mL, 63.2 mmol), and 10.0 mL of dry THF was stirred for 2 dat 25°C in a 100 mL round bottom flask protected with a CaCl2 tube. The reaction mixture was pouredinto 100 mL of ether and chilled in the refrigerator. To a mixture of 4.2 g of lithium bromide in 100 mLof DMSO was added 1.0 g of the above isouronium salt and 100 mL of pentane. The mixture wascooled and maintained below 20°C. Then 100 mL of an aqueous sodium hypobromite solution wasadded dropwise with stirring over 30 min. [The NaOBr solution was prepared by dropwise addition of7.0 mL of bromine to a cold (-5°C) solution of 40 g of sodium bromide and 13.0 g of sodium hydroxidein 100 mL of water.] The reaction mixture was then transferred to a separatory funnel and the aqueouslayer drained. The pentane phase was washed with cold brine and then dried over CaCl2 The pentanesolution was then concentrated to ~10 mL on the rotary evaporator and chromatographed over silicagel with pentane eluent. 3-Benzyloxy-3-bromodiazirine. UV (λmax, pentane) 348 nm. 1H NMR (δ,CDCl3): 7.40-7.28 (m, 5H, phenyl), 4.88 (s, 2H, CH2). 13C NMR (δ, CDCl3): 134.1, 128.8, 128.7,128.4. 70.6, 60.0.


SciFinder® Page 22

88%

Overview

Steps/Stages Notes

1.1 R:Bromosuccinimide, R:PPh3, 10 s 1) green chemistry, microwave irradiation, nosolvent, Reactants: 1, Reagents: 2, Steps: 1,Stages: 1, Most stages in any one step: 1

ReferencesAn efficient and fast method for thepreparation of benzylic bromidesBy Lee, Jong Chan, Hwang, Eui YongFrom Synthetic Communications, 34(16),2959-2963; 2004


68%

Overview

Steps/Stages Notes

1.1 R:

R:p-MeC6H4SO3H,

S:PhMe, 3 min, 200°C, 200 Pa 1) microwave irradn., thermal, high pressure,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesIonic liquids as reagents and solvents inconjunction with microwave heating: rapidsynthesis of alkyl halides from alcohols andnitriles from aryl halidesBy Leadbeater, Nicholas E. et alFrom Tetrahedron, 59(13), 2253-2258; 2003


SciFinder® Page 23

41. Single Step

97%

Overview

Steps/Stages Notes

1.1 R:SOBr2, S:355-42-0, S:PhMe, 14 h, rt 1) yield depends on reaction conditions,Reactants: 1, Reagents: 1, Solvents: 2, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesFluorous Solvent as a New Phase-ScreenMedium between Reagents and Reactants inthe Bromination and Chlorination of AlcoholsBy Nakamura, Hiroyuki et alFrom Organic Letters, 5(8), 1167-1169; 2003

Experimental ProcedureGeneral/Typical Procedure: General Procedure for Phase-Vanishing Bromination of Alcohols usingSOBr 2 (Table 1, entry 1). FC-72 (perfluorohexane, 2 mL) was placed in a test tube and thionyl bromide(0.12 mL, 1.5 mmol) was introduced slowly by using a glass pipette. The heavier thionyl bromide (d =2.68) sank to the bottom, forming two layers. The slow addition of benzyl alcohol 1a (54 mg, 0.5 mmol)dissolved in toluene (2 mL) formed a triphasic system. The reaction progress in the upper toluene layerwas monitored by GC analysis. Benzyl alcohol 1a was consumed for 14 h and the toluene layer wasdecanted, washed with water, dried over anhydrous MgSO4 , and then concentrated. Purification byshort column chromatography on silica gel with hexane. Compound no 2a.14 hours, benzyl bromide 2ain 97% yield (83 mg, 0.49 mmol).


70%

Overview

Steps/Stages Notes

SciFinder® Page 24

1.1 R:Bu4N+•Br-, R:DDQ, R:PPh3, S:CH2Cl2, rtReactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesTriphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective andneutral system for the facile conversion ofalcohols, thiols and selenols to alkyl halides inthe presence of halide ionsBy Iranpoor, N. et alFrom Tetrahedron, 58(43), 8689-8693; 2002


98%

Overview

Steps/Stages Notes

1.1 R:Cyanurictrichloride, R:NaBr, R:DMF, S:CH2Cl21) chemoselective, Reactants: 1, Reagents: 3,Solvents: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesAn Efficient Route to Alkyl Chlorides fromAlcohols Using the Complex TCT/DMFBy De Luca, Lidia et alFrom Organic Letters, 4(4), 553-555; 2002


98%

Overview

Steps/Stages Notes

SciFinder® Page 25

1.1 R:Et3SiH, R:PdCl2Reactants: 2, Reagents: 2, Steps: 1, Stages:2, Most stages in any one step: 2

ReferencesThe versatile behavior of the PdCl2/Et3SiHsystem. Conversion of alcohols to thecorresponding halides and alkanesBy Ferreri, C. et alFrom Journal of Organometallic Chemistry,554(2), 135-137; 1998


94%

Overview

Steps/Stages Notes

1.1 R:CBr4, C:Cu, C:Fe, C:CuBr, C:1,10-Phenanthroline, S:DMF

1.2 R:HCl, S:H2O

1) catalyst formed in-situ, other solvents givelower yields, Reactants: 1, Reagents: 2,Catalysts: 4, Solvents: 2, Steps: 1, Stages: 2,Most stages in any one step: 2

ReferencesA New Preparative Route to Organic Halidesfrom Alcohols via the Reduction ofPolyhalomethanesBy Leonel, E. et alFrom Journal of Organic Chemistry, 62(20),7061-7064; 1997


95%

Overview

Steps/Stages Notes

SciFinder® Page 26

1.1 R:NaBr 1) microwave, NaBr doped on K-10 clay,Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1

ReferencesSelective preparation of benzylic bromides indry media coupled with microwave irradiationBy Kad, Goverdhan L. et alFrom Tetrahedron Letters, 38(6), 1079-1080;1997


81%

Overview

Steps/Stages Notes

1.1 R:Bromosuccinimide, R:PPh3, S:Dioxane Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesFormation of acyl bromides from carboxylicacids and N-bromosuccinimide; somereactions ofbromocyanotriphenylphosphoraneBy Fryeyen, PaulFrom Phosphorus, Sulfur and Silicon and theRelated Elements, 102(1-4), 253-9; 1995

CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactionsfrom CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformationsdatabase compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproducedunder license. All Rights Reserved.48. 2 Steps

Overview

Steps/Stages Notes

SciFinder® Page 27

1.1 R:SnCl42.1 R:BBr3

Reactants: 1, Reagents: 2, Steps: 2, Stages:2, Most stages in any one step: 1

ReferencesA simple method for the conversion ofadamantyl, benzyl and benzyhydryl alcoholsto their corresponding bromides and chloridesand the transhalogenation of adamantyl,benzyl, benzhydryl and tertiary alkyl bromidesand chloridesBy Amrollah-Madjdabadi, A. et alFrom Synthesis, (8), 614-16; 1989


93%

Overview

Steps/Stages Notes

1.1 R:BBr3Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1

ReferencesA simple method for the conversion ofadamantyl, benzyl and benzyhydryl alcoholsto their corresponding bromides and chloridesand the transhalogenation of adamantyl,benzyl, benzhydryl and tertiary alkyl bromidesand chloridesBy Amrollah-Madjdabadi, A. et alFrom Synthesis, (8), 614-16; 1989


87%

Overview

SciFinder® Page 28

Steps/Stages Notes

1.1 R:PBr3, S:Et2OReactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesEffect of structure factors on the rate ofbimolecular homolytic substitution at carbonin benzylcobalt complexesBy Dneprovskii, A. S. et alFrom Zhurnal Organicheskoi Khimii, 24(5),923-9; 1988


80%

Overview

Steps/Stages Notes

Reactants: 1, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesCollision-induced dissociations of aryl-substituted alkoxide ions. Losses ofdihydrogen and rearrangement processesBy Raftery, Mark J. et alFrom Journal of the Chemical Society, PerkinTransactions 2: Physical Organic Chemistry(1972-1999), (4), 563-9; 1988


88%

SciFinder® Page 29

Overview

Steps/Stages Notes

1.1 R:Triflicacid, R:Bu4N+•Br-, S:CH2Cl2Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesConversion of alcohols into alkyl bromidesand iodides via O-alkylisoureasBy Collingwood, Stephen P. et alFrom Tetrahedron Letters, 28(38), 4445-8;1987


100%

Overview

Steps/Stages Notes

1.1 R:PBr3, S:ClCH2CH2Cl Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesPrimary and secondary kinetic deuteriumisotope effects and transition-state structuresfor benzylic chlorination and bromination oftolueneBy Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 109(16), 4926-30; 1987


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Overview

Steps/Stages Notes

1.1 R:

R:BF3-Et2O,

S:CHCl3 Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesBoron trifluoride etherate/halide ion, a novelreagent for the conversion of allyl, benzyl andtertiary alcohols to the halidesBy Mandal, Arun K., Mahajan, S. W.From Tetrahedron Letters, 26(32), 3863-6;1985


Overview

Steps/Stages Notes

1.1 R:HBr, S:H2OReactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesAromatic rearrangements in the benzeneseries. Part 4. Intramolecularity of both theortho- and para-rearrangements of benzylphenyl ether as shown by labelingexperimentsBy Hart, Lionel S., Waddington, Catherine R.From Journal of the Chemical Society, PerkinTransactions 2: Physical Organic Chemistry(1972-1999), (10), 1607-12; 1985


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Overview

Steps/Stages Notes

1.1 R:EtO2CN=NCO2Et, R:PPh3, R:LiBr, S:THF Reactants: 1, Reagents: 3, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesA convenient preparation of alkyl halides andcyanides from alcohols by modification of theMitsunobu procedureBy Manna, Sukumar et alFrom Synthetic Communications, 15(8), 663-8; 1985


Overview

Steps/Stages Notes

1.1 R:HBr, S:Benzene Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesIntramolecular kinetic deuterium isotopeeffects on microsomal hydroxylation andchemical chlorination of toluene-α-d1 andtoluene-α,α-d2By Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 107(24), 7164-7; 1985


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58. Single Step

Overview

Steps/Stages Notes

1.1 R:HBr, S:Benzene Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesIntramolecular kinetic deuterium isotopeeffects on microsomal hydroxylation andchemical chlorination of toluene-α-d1 andtoluene-α,α-d2By Hanzlik, Robert P. et alFrom Journal of the American ChemicalSociety, 107(24), 7164-7; 1985


80%

Overview

Steps/Stages Notes

Reactants: 2, Steps: 1, Stages: 1, Most stagesin any one step: 1

ReferencesConversion of alcohols into alkyl bromidesusing polymer-supported triphenylphosphinedibromide and polymer-supportedtriphenylphosphine and carbon tetrabromideBy Hodge, Philip, Khoshdel, EzzatollahFrom Journal of the Chemical Society, PerkinTransactions 1: Organic and Bio-OrganicChemistry (1972-1999), (2), 195-8; 1984

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82%

Overview

Steps/Stages Notes

1.1 R:PBr3 (polymer-bound) Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1

ReferencesPolymer-bonded Lewis acids in organicsynthesis: conversion of carboxylic acids intoacyl chlorides and of alcohols into alkylchlorides or bromides by polymer-bondedphosphorus reagentsBy Cainelli, Gianfranco et alFrom Synthesis, (4), 306-8; 1983


100%

Overview

Steps/Stages Notes

1.1 R:Me3SiCl, S:MeCN 1) Classification: Substitution; Bromination; #Conditions: Me3SiCl + LiBr; MeCN; Rf / N2,Reactants: 1, Reagents: 1, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesChlorotrimethylsilane/lithium bromide andhexamethyldisilane/pyridinium bromideperbromide: effective and selective reagentsfor the conversion of alkyl (cycloalkyl andaralkyl) alcohols into bromidesBy Olah, George A. et alFrom Journal of Organic Chemistry, 45(9),1638-9; 1980

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100%

Overview

Steps/Stages Notes

1.1 R:Py•HBr3, R:(Me3Si)2NH, S:CHCl31) Classification: Substitution; Bromination; #Conditions: py.HBr3; HMDS; CHCl3 dry;30mn; # Comments: reference Synthesis(1981) p325; yield in range 78% to 100%,Reactants: 1, Reagents: 2, Solvents: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesChlorotrimethylsilane/lithium bromide andhexamethyldisilane/pyridinium bromideperbromide: effective and selective reagentsfor the conversion of alkyl (cycloalkyl andaralkyl) alcohols into bromidesBy Olah, George A. et alFrom Journal of Organic Chemistry, 45(9),1638-9; 1980


Overview

Steps/Stages Notes

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1.1 R:NH4Br, C:HF-pyridine Reactants: 1, Reagents: 1, Catalysts: 1, Steps:1, Stages: 1, Most stages in any one step: 1

ReferencesSynthetic methods and reactions. 63.Pyridinium poly(hydrogen fluoride) (30%pyridine-70% hydrogen fluoride): aconvenient reagent for organic fluorinationreactionsBy Olah, George A. et alFrom Journal of Organic Chemistry, 44(22),3872-81; 1979


Overview

Steps/Stages Notes

1.1 R:HBr Reactants: 1, Reagents: 1, Steps: 1, Stages:1, Most stages in any one step: 1

ReferencesSynthesis of 14C-methyl benzyl nitrosamineand methyl 14C-benzyl nitrosamineBy Skipper, Paul L.From Journal of Labelled Compounds andRadiopharmaceuticals, 15(Suppl. Vol.), 575-9; 1978


80% (80:20 ) 80% (80:20 )

Overview

Steps/Stages Notes

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1.1 R:CBrCl3, C:Cu, C:Fe, C:CuBr, C:1,10-Phenanthroline, S:DMF

1.2 R:HCl, S:H2O

1) catalyst formed in-situ, other solvents givelower yields, Reactants: 1, Reagents: 2,Catalysts: 4, Solvents: 2, Steps: 1, Stages: 2,Most stages in any one step: 2

ReferencesA New Preparative Route to Organic Halidesfrom Alcohols via the Reduction ofPolyhalomethanesBy Leonel, E. et alFrom Journal of Organic Chemistry, 62(20),7061-7064; 1997


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