Aniline → Methyl 4-anilino-2-(4-fluoroanilino)benzoate

Participants

Reaction Steps

To toluene 2.0 mL suspension of methyl 2-(4-fluoroanilino)-4-iodobenzoate 0.20 g, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 10 mg, palladium acetate 4 mg and cesium carbonate 0.35 g was added aniline 0.074 mL, and it was heated and refluxed under nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 10 mg and palladium acetate 4 mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, insoluble matter was filtrated, 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 4-anilino-2-(4-fluoroanilino)benzoate 0.13 g of pale yellow solid.

Provenance & Evidence