Ammonium Chloride → 1-(4-Bromo-3-methylphenyl)ethanol

Participants

Reaction Steps

A solution of 4-bromo-3-methylbenzaldehyde (4 g, 20 mmol) in tetrahydrofuran (40 mL) was cooled to 0° C. then methylmagnesium bromide (20 mL, 1N in tetrahydrofuran) was dropped and the mixture was stirred at 0° C. to room temperature for 2 hours. Ammonium chloride aqueous (40 mL) was added and the mixture was extracted with dichloromethane (3*20 mL), dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give 1-(4-bromo-3-methylphenyl)ethanol as a colorless oil (4.0 g, 93%).

Provenance & Evidence