Boron tribromide → 2',6'-Dichloro-5-fluorobiphenyl-2-ol

Participants

Reaction Steps

To a solution of 2′,6′-dichloro-5-fluoro-2-methoxybiphenyl (12.44 g, 46 mmol) in methylene chloride (200 mL) was added boron tribromide (10.8 mL, 92 mol) at −78° C. The resulting mixture was stirred at −78° C. to room temperature overnight. The reaction mixture was poured into the ice-NH4OH and extracted with methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography with 10–40% ethyl acetate in hexanes afforded 11.63 g (98%) of 2′,6′-dichloro-5-fluorobiphenyl-2-ol as a colorless oil. MS (ES) m/z 255.1([M−H]−).

Provenance & Evidence