Toluene → Tert-butyl 2-(4-fluoroanilino)-4-phenethylbenzoate

Participants

Reaction Steps

To toluene 10 mL solution of tert-butyl 2-amino-4-phenethylbenzoate 1.0 g were added 1-fluoro-4-iodobenzene 0.98 mL, cesium carbonate 2.2 g, palladium acetate 8 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 21 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 21 mg were added, and it was heated and refluxed under nitrogen atmosphere for 10 hours. After the reaction mixture was cooled to room temperature, water was added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to give tert-butyl 2-(4-fluoroanilino)-4-phenethylbenzoate 0.80 g of pale yellow oil.

Provenance & Evidence