Diisobutylaluminum hydride → 2-Bromo-5-(hydroxymethyl)phenol

Participants

Reaction Steps

To a suspension of 4-bromo-3-hydroxybenzoic acid methyl ester 70 (6.97 g, 30.2 mmol) in dichloromethane (360 mL) at 0° C. was added DIBALH (100 mL of a 1 M in toluene, 100 mmol) portionwise. Significant gas evolution was observed. The resultant mixture was warmed to room temperature and stirred for 2.75 h. After this time, the reaction mixture was quenched by the addition of saturated aqueous sodium potassium tartrate (600 mL) and saturated aqueous ammonium chloride (100 mL). The resultant biphasic mixture was stirred vigorously for 2 h, and then extracted with dichloromethane (3×). The organic layers were dried over Na2SO4 and filtered, to give 71. 1H NMR (400 MHz CDCl3) δ: 1.70 (br s, 1H), 4.64 (d, J=4.5 Hz, 2H), 5.55 (br s, 1H), 6.82 (dd, J=8.0 Hz, 2.0 Hz, 1H), 7.04 (d, J=2.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H). MS (EI) m/z (M−H−) 201.

Provenance & Evidence