4-Fluoroaniline → Methyl 2-(4-fluoroanilino)-4-methoxybenzoate

Participants

Reaction Steps

To toluene 30 mL suspension of methyl 2-iodo-4-methoxybenzoate 2.7 g, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 58 mg, palladium acetate 20 mg and cesium carbonate 6.0 g was added 4-fluoroaniline 1.3 mL, and it was heated and refluxed under nitrogen atmosphere for 5 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 2-(4-fluoroanilino)-4-methoxybenzoate 2.2 g of white solid.

Provenance & Evidence