Methanol → 1-(4'-Chloro-4-fluoro-biphen-2-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

1-(2-Bromo-5-fluoro-phenyl)-ethanone (868 mg, 4 mmol), p-chlorophenylboronic acid (768 mg, 1.2 eq.), and tetrakis (triphenylphosphine)palladium(0) (473 mg, 0.1 eq.), were dissolved in 25 mL toluene, 6 mL methanol and 2.5 mL sat. sodium bicarbonate solution. After degassing/sonicating the solution, the sealed reaction vessel was heated to 80° C. overnight. The cooled solution was separated between ethyl acetate and water; the aqueous phase extracted two more times with ethyl acetate, and the organic fractions were combined, dried with sodium sulfate and evaporated. Silica gel chromatography (5:1 hexanes/ethyl acetate) gave 1-(4′-chloro-4-fluoro-biphen-2-yl)-ethanone (821 mg).

Provenance & Evidence