Water → [3-Bromo-5-(trifluoromethyl)phenyl]methanol

HRID 355369

Reaction equation

HRID 355369 reaction equation
[BH4-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7](OC)=[O:8].O>CCOCC.[NH4+].[Cl-]>[Br:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1)[CH2:7][OH:8]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoate

Product 1

HCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanolYield 94.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Lithium borohydride (22 0mg) was added in a single portion to a stirred solution of methyl 3-bromo-5-(trifluoromethyl)benzoate (2.46 g) in ether (60 ml) containing water (156 ml). The resulting solution was stirred for 4 hours at room temperature, at which point the reaction mixture was diluted with saturated aqueous NH4Cl solution (50 ml). The organic layers were separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to give 3-bromo-5-(trifluoromethyl)benzyl alcohol as a clear oil (2.1 g).1H NMR (360 MHz,CDCl3) δ 1.83 (1H, br s), 4.76 (2H,s), 7.47 (1H, s), 7.56 (1H, s), 7. 68 (1H, s).

Workup

  1. customThe organic layers were separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-917a6a113bd240b086d0b393ab3ee70e
Source dataset
uspto-grants-1998_11
Patent number
US05830892

Linked notes

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