1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester → (5-Bromo-1,3-phenylene)dimethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-isophthalic acid dimethyl ester (4.54 g, 16.63 mmol) in methylene chloride (50 mL) cooled to 0° C. under argon was added diisobutylaluminum hydride (80 mL, 80 mmol, 1 M in toluene) via syringe. The reaction was quenched by Rochelle salt solution after 1 h of stirring at 0° C. The biphasic mixture was then stirred at room temperature for 12 h before work-up. The product was extracted with diethyl ether (2×50 mL). The organic layers were washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo to afford (3-bromo-5-hydroxymethyl-phenyl)-methanol as a white solid (3.582 g, 99%).

Provenance & Evidence