Hydrochloric Acid → 4-Bromo-3-trimethylsilylanisole

Participants

Reaction Steps

To a solution of 2,4-dibromoanisole (13.3 g, 50 mmol) in diethyl ether (50 ml) at 0° C. was added over 20 min 1.5M butyllithium (33.4 ml) and the reaction was allowed to react 15 min at 0° C. Then trimethylsilylchloride (5.43 g, 50 mmol) in diethyl ether (20 ml) was added over 10 min and the resulting mixture was stirred 18 hours at room temperature. At 0° C. 3N HCl (50 ml) was added and the organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated. 4-Bromo-3-trimethylsilylanisole was purified by chromatography on silica gel (eluted with cyclohexane) as a colorless oil.

Provenance & Evidence