General procedure for the synthesis of 3-iodo-4-methoxyaniline from 2-iodo-4-nitroanisole: To a 250 mL round-bottomed flask were added 2-iodo-1-methoxy-4-nitrobenzene (6 g, 21.50 mmol, 1.00 eq.), iron powder (3.61 g, 64.50 mmol, 3.00 eq.), ammonium chloride (3.42 g, 63.94 mmol , 3.00 equiv), ethanol (50 mL) and water (10 mL). The reaction mixture was stirred at 85 °C for 1 hour. Upon completion of the reaction, the solid insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The brown solid product 3-iodo-4-methoxyaniline (5.35 g, 100% yield) was obtained. The product was analyzed by liquid chromatography-mass spectrometry (LC-MS): (electrospray ionization, m/z) retention time (RT) = 0.847 min, LCMS 53: m/z = 250 [M + 1].
