Reaction #2075717

Reaction equation

Sodium borohydride

1-(5-bromo-2-chlorophenyl)ethanone

→

title compound

Yield 99.3%

1-(5-Bromo-2-chlorophenyl)-ethanol

Yield 99.3%

Solvents

methanol

Conditions

Workup

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

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 room 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, 42.5 mmol, 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).

Source