2-(4-Bromoanilino)-1-phenyl-1-ethanone → 2-(4-Bromoanilino)-1-phenylethan-1-ol

Participants

Reaction Steps

A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil.

Provenance & Evidence