The general procedure for the synthesis of 5-chloro-3-iodo-2-methyl-3-nitrobenzene from 5-chloro-1-iodo-2-methyl-3-nitrobenzene was as follows: 5-chloro-1-iodo-2-methyl-3-nitrobenzene (3.0 g, 10.1 mmol) was mixed with tin(II) chloride dihydrate (9.1 g, 40.4 mmol) in acetic acid (10 mL) and stirred for 1 hour at room temperature. After the reaction was completed, the reaction mixture was diluted with ether. The mixture was cooled to 0°C and 50% aqueous sodium hydroxide solution was added slowly. The lumpy white solid generated in the reaction was removed by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 4:1, v/v) to afford 5-chloro-3-iodo-2-methylaniline (1.81 g, 67% yield) as a light yellow solid.1H NMR (400 MHz, CDCl3) δ 7.25 (d, 1H), 6.64 (d, 1H), 3.78 (br s 2H), 2.28 (s, 3H).
