3-Nitrophenylboronic Acid → Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of methyl 4-bromobenzoate (1.00 g) and 3-nitrophenylboronic acid (800 mg) in dioxane (20 mL) was added tetrakis(triphenylphosphine)palladium(0) (165 mg) and solid sodium carbonate (710 mg). The mixture was heated at 85° C. overnight, cooled to room temperature and partitioned between dichloromethane (100 mL) and 2 M aqueous sodium carbonate (50 mL) containing concentrated ammonium hydroxide (5 mL). The aqueous layer was further extracted twice with dichioromethane. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was absorbed onto silica and chromatographed on silica gel eluting with 6:94 ethyl acetate in hexane to provide the title compound (198 mg) as a white solid

Provenance & Evidence