Methanol → Methyl 4'-hydroxy-3'-methyl[1,1'-biphenyl]-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 1.0 M BBr3 solution in CH2Cl2 (3.4 mL, 3.40 mmol) was added to an ice-cold solution of methyl 4′-methoxy-3′-methyl-[1,1′-biphenyl]-3-carboxylate (345 mg, 1.35 mmol) in CH2Cl2 (13 mL). The reaction mixture was stirred at 25° C. for 2 h then was cooled to 0° C. MeOH (5 mL) was added and the mixture was stirred at 0° C. for 15 min then was extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane, 10 to 15%) to yield the title compound (278 mg, 85% yield) as a white solid.

Provenance & Evidence