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

Participants

Reaction Conditions

Reaction Steps

1-(2-Bromo-5-nitro-phenyl)-ethanone (1 g, 4 mmol; prepared similarly to the procedure described in Meisenheimer, J., Zimmermann P., and v. Kummer, U. Ann. der. Chem. 446, pp. 205-228), 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 (4:1 hexanes/ethyl acetate) gave 1-(4′-chloro-4-nitro-biphen-2-yl)-ethanone (962 mg).

Provenance & Evidence