Methanol → HCID 59627720, compound

Participants

Reaction Conditions

Reaction Steps

Tribromoborane (0.666 ml, 7.04 mmol) was added dropwise to methyl 1-(3,5-difluoro-4-methoxyphenyl)cyclopropanecarboxylate (Intermediate 28-4; 1.4216 g, 5.87 mmol) in dichloromethane (46.2 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 1 hour. The reaction mixture was added dropwise to methanol (11.87 mL, 293.45 mmol) (care reaction is vigorous and exothermic—MeOH kept in ice bath) 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 with MgSO4 and evaporated to afford crude product. The crude product was purified by flash silica chromatography, eluted at 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 1-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylate (0.657 g, 49.1%) as a white solid.

Provenance & Evidence