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

HRID 245270Notes

Reaction equation

HRID 245270 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-f66bb4034f54490aa9fd35a241ad41b3
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

Loading…