4-Fluoroiodobenzene → Methyl 2-(4-fluoroanilino)-4-((phenylthio)methyl)benzoate

Participants

Reaction Steps

To toluene 9.5 mL suspension of methyl 2-amino-4-((phenylthio)methyl)benzoate hydrochloride 0.96 g, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 19 mg, palladium acetate 7 mg and cesium carbonate 3.0 g was added 1-fluoro-4-iodobenzene 1.1 mL, and it was heated and refluxed under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, palladium acetate 7.0 mg was added to it, and it was heated and refluxed for 14 hours. After 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=20:1] to give methyl 2-(4-fluoroanilino)-4-((phenylthio)methyl)benzoate 0.48 g of pale yellow oil.

Provenance & Evidence