Hydrochloric Acid → 3-Bromo-5-hydroxybenzenemethanol

Participants

Reaction Steps

To a solution of 3-bromo-5-hydroxy-benzoic acid (5.0 g, 23.4 mmol) in 40 mL of THF was added a solution of 1M LiAlH4 (30 mL), and the resulting solution was heated to reflux for 2 h. After cooling to room temperature, the reaction mixture was poured on ice and acidified with 10% aq. HCl. The solution was then filtered under vacuum and the filtrate was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by column chromatography (Isco™ 120 g) using 50% ethyl acetate/hexanes as eluting solvents to afford the title compound as a white solid (1.7 g, 36% yield). HR-ES(−) calcd for C7H7O2Br [M−H]− 200.9556, observed 200.9557.

Provenance & Evidence