Sodium borohydride → 1-(5-Bromo-2-chlorophenyl)ethanol

HRID 2386118Notes

Reaction equation

HRID 2386118 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:10]([OH:12])[CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136281451-(5-Bromo-2-chlorophenyl)ethan-1-one

Product 1

HCID 587626441-(5-Bromo-2-chlorophenyl)ethanolYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H).

Workup

  1. customThe resulting bubbling white mixture
  2. customThe reaction mixture was quenched with acetone (50 mL)
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b74502a3ccdd40a196d394a41a5e514a
Source dataset
uspto-grants-2012_09
Patent number
US08268753B2

Reaction notes

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