Citric Acid → HCID 68962723, compound

Participants

Reaction Steps

To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.30 g were added 2-nitroaniline 0.17 g, cesium carbonate 0.53 g, tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, palladium acetate 4.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 20 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 2 hours. Tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, palladium acetate 4.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 20 mg were added to it, and it was heated and refluxed for 3 hours. Tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, palladium acetate 4.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 20 mg were added to it, and it was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, toluene, ethyl acetate and 10% citric acid aqueous solution were added to it, and 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, 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 tert-butyl 2-(4-fluoroanilino)-4-(2-nitroanilino)benzoate 0.35 g of a yellow solid.

Provenance & Evidence