Boron tribromide → 3-Hydroxyphenacyl bromide

Participants

Reaction Steps

To a stirred solution of 2-bromo-1-(3-methoxy-phenyl)-ethanone (Aldrich, 3.44 g, 15 mmol) in methylene chloride (20 mL) at −10° C., boron tribromide (Aldrich, 16.5 mmol, 1M solution in CH2Cl2, 16.5 mL) was added slowly and the mixture was stirred for 1.5 hours. The reaction was quenched with ice water and the organic layer was separated. The aqueous layer was extracted with EtOAc and the extracts were combined and dried with sodium sulfate. Removal of solvent gave a greenish solid which was purified by chromatography (EtOAc/Hexane, 25%) gave an off-white solid. 770 mg, 24%. The compound was used directly for the next step.

Provenance & Evidence