Toluene → HCID 57667801, compound

Participants

Reaction Steps

To toluene 12 mL solution of methyl 2-amino-4-bromobenzoate 1.2 g were added 1-fluoro-4-iodobenzene 1.5 mL, cesium carbonate 3.4 g, palladium acetate 12 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32 mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and 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 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g of pale yellow solid.

Provenance & Evidence