Dichloromethane → 2-[4-(3,4-Dichlorophenyl)phenylamino]benzoic acid

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Reaction Steps

A mixture of 3,4-dichlorophenylboronic acid (880 mg, 2.3 mmol), 2-[(4-iodophenyl)amino]benzoic acid (339 mg, 1 mmol), PdCl2.dppf.CH2Cl2 [1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, complexed with dichloromethane (1:1)] (67 mg, 0.082 mmol), K2CO3 (829 mg, 6 mmol), and H2O (2 mL) in dioxane (15 mL) was heated to reflux for 1 hour. The reaction mixture was diluted with EtOAc and filtered. The filtrate was treated with 1N HCl, washed with H2O, brine, dried (Na2SO4), and concentrated in vacuum to give a yellow solid. Purification by flash chromatography (silica gel, 10% MeOH/CH2Cl2) yielded 272 mg (0.76 mmol, 76%) of the desired product. mp>220° C.

Provenance & Evidence