Dichloromethane → HCID 59627740, compound

Participants

Reaction Steps

Boron tribromide (8.02 mL, 84.87 mmol) was added dropwise to 2-(4-methoxy-3-(trifluoromethyl)phenyl)acetic acid (3.31 g, 14.13 mmol) in dichloromethane (250 mL) while maintaining the temperature below 10° C. After complete addition the reaction mixture was removed from the ice bath and allowed to stir at ambient temperature under nitrogen for 90 minutes. The reaction mixture was added dropwise to ice cold methanol (150 mL) and the mixture was stirred at ambient temperature for a further 40 minutes. The reaction mixture was evaporated to afford to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(4-hydroxy-3-(trifluoromethyl)phenyl)acetate (1.100 g, 33.2%) as a pale yellow oil.

Provenance & Evidence