Sodium Hydroxide → 2',3',4',5,5',6'-Hexafluoro-[1,1'-biphenyl]-2-ol

Participants

Reaction Conditions

Reaction Steps

A 1.0 M boron tribromide solution in dichloromethane (24 mL, 24 mmol, 2.4 equiv) was added dropwise over 30 minutes, at −78° C., to a solution of compound 2 (3.0 g, 10.2 mmol, 1 equiv) in dichloromethane (100 mL). The reaction was stirred at −78° C. for 3 hours, when 1H NMR indicated that the reaction was complete. The reaction was poured into saturated sodium bicarbonate (200 mL) and the pH was adjusted to 8 with 10% sodium hydroxide. The layers were separated, then the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified over silica gel (40 g), eluting with a gradient of 0 to 20% ethyl acetate in heptanes to give 2′,3′,4′,5,5′,6′-hexafluoro-[1,1′-biphenyl]-2-ol (3) (2.3 g, 80% yield) as a white solid.

Provenance & Evidence