Diisobutylaluminumhydride → (2-Bromo-4,5-difluorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromo-4,5-difluoro-benzoic acid methyl ester (1.45 g, 5.78 mmol) in toluene (42 mL) was cooled at −78° C. under nitrogen. Diisobutylaluminum hydride (1 M in toluene) (7.51 mL, 7.51 mmol) was added drop-wise over 20 minutes. The reaction mixture was stirred at −78° C. for another hour, and then allowed to warm to room temperature overnight. The reaction mixture was then cooled to 0° C. and quenched with ethyl acetate, followed by addition of saturated Rochelle's salt solution. The biphasic slurry was then allowed to warm to room temperature and stirred for 2 hours. The organic layer was collected, dried over sodium sulfate, filtered, and concentrated to afford crude (2-bromo-4,5-difluoro-phenyl)-methanol (1.55 g, 90%), which was used in the next step without further purification.

Provenance & Evidence