Acetic Acid → (R)-1-(4-Bromo-3-methylphenyl)ethan-1-ol

Participants

Reaction Steps

A mixture of 1-(4-bromo-3-methylphenyl)ethanone (27.3 g, 128 mmol) and (S)-2-Methyl-CBS-oxazaborolidine (3.6 g, 12.8 mmol) in dichloromethane (500 mL) was added dimethylsulfide-borane (64 mL, 2M in tetrahydrofuran) dropwise at −20° C. and maintained at the same temperature for 2 hours. Acetic acid (15 mL) was added to quench the reaction. The resultant mixture was concentrated to give a residue. Then the mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give (R)-1-(4-bromo-3-methylphenyl)ethanol (19.6 g, 71%)

Provenance & Evidence