Boron tribromide → 2',3',4',5',6'-Pentafluoro-5-methyl-[1,1'-biphenyl]-2-ol

Participants

Reaction Steps

A 1.0 M boron tribromide solution in dichloromethane (67.3 mL, 67.3 mmol, 2 equiv) was added dropwise, at −78° C., over 30 minutes to a solution of compound 6 (9.7 g, 33.65 mmol, 1 equiv) in anhydrous dichloro-methane (300 mL). The reaction was warmed to room temperature, when LCMS indicated that the reaction was complete. The reaction was quenched with ice-water (200 mL). The layers were separated and 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 on an AnaLogix 65-200 g column, eluting with a gradient of 0 to 20% ethyl acetate in heptanes to give 2′,3′,4′,5′,6′-pentafluoro-5-methyl-[1,1′-biphenyl]-2-ol (7) (8.15 g, 88% yield) as a light-brown oil.

Provenance & Evidence