Potassium Phosphate, Tribasic → Methyl 3-ethoxy-4'-fluorobiphenyl-4-carboxylate

Participants

Reaction Steps

Palladium acetate (0.484 g) was added to a mixture of methyl 2-hydroxy-4-iodobenzoate (6.00 g), tripotassium phosphate (13.7 g), (4-fluorophenyl)boronic acid (6.04 g), tricyclohexylphosphine (20% toluene solution, 7.66 mL), toluene (30 mL), and water (15 mL), and the resultant mixture was stirred at 90° C. for 1.5 hours in an argon atmosphere. The reaction mixture was allowed to cool to room temperature, and then, the organic layer was separated. The aqueous layer was subjected to extraction with ethyl acetate. Combined organic layers were washed with saturated saline, then dried over anhydrous magnesium sulfate, and then passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure. Iodoethane (2.59 mL) was added to a DMF (50 mL) suspension of the obtained residue and potassium carbonate (4.47 g), and the mixture was stirred at 80° C. for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (5.92 g).

Provenance & Evidence