38257-52-2

624-38-4

122-39-4

38257-52-2

GENERAL STEPS: 1,4-Diiodobenzene (396 mg, 1.2 mmol), diphenylamine (169 mg, 1 mmol), cuprous iodide (CuI, 19 mg, 0.1 mmol), phenanthroline (28.2 mg, 0.12 mmol) and potassium hydroxide (224 mg) were added to anhydrous toluene (20 mL) under nitrogen protection. The reaction mixture was heated to 120 °C and the reaction was stirred at this temperature for about 12 hours. Upon completion of the reaction, water (30 mL) was added to quench the reaction. The reaction mixture was extracted three times with dichloromethane (CH2Cl2, 30 mL), the organic phases were combined and dried overnight with anhydrous magnesium sulfate. The organic solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with petroleum ether as eluent to afford N-(4-iodophenyl)-N-phenylaniline (315.4 mg, 85%) as white powder. Melting point >300°C; 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 2H), 7.28 (m, 4H), 7.08 (m, 6H), 6.83 (d, 2H); MS (ESI): m/z, calculated value for C18H14IN: 371.21, measured value: 372.02 [M + H]+.