4'-Bromo-3-chloropropiophenone → 4-Bromo-alpha-(2-chloroethyl)benzenemethanol

Participants

Reaction Steps

To a solution of sodium borohydride (3.8 g, 100 mmol) in tetrahydrofuran (100 mL) was added a solution of 1-(4-bromo-phenyl)-3-chloro-propan-1-one (25 g, 100 mmol) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated to about 50 mL under reduced pressure and diluted with water. Extractive workup was performed with ethyl acetate and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate=3/1 as an eluant) to yield 1-(4-bromo-phenyl)-3-chloro-propan-1-ol (25 g, 100 mmol, 100%) as yellow oil.

Provenance & Evidence