Diisobutylaluminum hydride → 4-(Bromomethyl)benzyl alcohol

Participants

Reaction Steps

To a solution of 4-bromomethyl-benzoic acid methyl ester (5 g, 21.82 mmol) in DCM (200 mL) is added DIBAL-H (1.0 M in hexane, 54.56 mL, 54.56 mmol) drop wise at −78° C. The reaction mixture is allowed to warm to room temperature and stirred for 16 hours. The reaction mixture is quenched with sodium potassium tartrate (10% solution, 8 mL) and diluted with DCM (100 mL). The combined organic layer is washed with water (50 mL), brine (25 mL), dried over sodium sulfate, and evaporated to give the title compound as an off white solid (3.5 g, 81%). 1H NMR (400 MHz, CDCl3) δ 7.23-7.21 (m, 2H), 7.4-7.3 (m, 2H), 4.5-4.3 (bs, 2H), 4.68 (s, 2H).

Provenance & Evidence