Toluene → HCID 68959360, compound

Participants

Reaction Steps

To toluene 7.5 mL solution of tert-butyl 2-amino-4-phenylbenzoate 0.50 g were added 1-fluoro-4-iodobenzene 0.22 mL, cesium carbonate 1.3 g, palladium acetate 4.3 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 12 mg at room temperature, and it was heated and refluxed for 4 hours. After the reaction mixture was cooled to room temperature, palladium acetate 4.3 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 12 mg were added to it, and it was heated and refluxed for 13 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. 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, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-(4-fluoroanilino)-4-phenylbenzoate 0.44 g of brown oil.

Provenance & Evidence