Toluene → Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Participants

Reaction Steps

To toluene 15 mL solution of tert-butyl 2-amino-4-bromobenzoate 1.0 g were added 1-fluoro-4-iodobenzene 0.85 mL, cesium carbonate 3.6 g, palladium acetate 8 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 23 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, palladium acetate 8 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 23 mg were added to it, it was heated and refluxed under nitrogen atmosphere for 8 hours. After the reaction mixture was cooled to room temperature, water was added to it, insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=20:1] to give tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.55 g of pale yellow oil.

Provenance & Evidence