Methanol → Methyl 2-(3,5-difluoro-4-hydroxyphenyl)acetate

Participants

Reaction Steps

Tribromoborane (2.357 mL, 24.93 mmol) was added dropwise to 2-(3,5-difluoro-4-methoxyphenyl)acetic acid (0.84 g, 4.16 mmol) in dichloromethane (5 mL) at ambient temperature under nitrogen. The resulting solution was stirred at ambient temperature for 16 hours. Methanol (8.41 mL, 207.76 mmol) was added dropwise (—care reaction is vigorous and exothermic—mixture maintained a reflux during the addition) and the mixture was stirred for a further 20 minutes. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and washed sequentially with saturated NaHCO3 (50 mL) and water (50 mL). The organic layer was dried by passing through a phase seperating cartridge and evaporated to afford desired product methyl 2-(3,5-difluoro-4-hydroxyphenyl)acetate (0.660 g, 79%).

Provenance & Evidence