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

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).

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

ORD record

ord-8feae0ab500d4dbfb65229e4b782c8a7

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609592B2