3-Bromo-4-methoxybenzoic acid → (3-Bromo-4-methoxyphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-4-methoxy-benzoic acid (8 g, 34.62 mmol) in diethyl ether (120 mL) cooled to 0° C. was added lithium aluminum hydride (1.49 g, 38.08 mmol) in several portions. At the end of addition, the reaction mixture was stirred at 0° C. for 15 min before the icebath was removed. The reaction was continued at room temperature for 12 h. It was cooled back to 0° C. and water (2-5 mL) was carefully added to quench the excess lithium aluminum hydride. Sodium hydroxide (5% solution, 5-10 mL) was then added and the layers were separated after 1 h of stirring. The product was extracted with diethyl ether (2×100 mL). The organic layers were washed with sodium bicarbonate solution (1×10 mL), brine (1×10 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 40% ethyl acetate in hexanes yielded (3-bromo-4-methoxy-phenyl)-methanol as a white solid (6.262 g, 83%).

Provenance & Evidence