55215-55-9

335349-66-1

55215-55-9

General procedure for the synthesis of 1,4-diiodo-2-methoxy-5-nitrobenzene from 4-iodo-5-methoxy-2-nitroaniline: 4-iodo-5-methoxy-2-nitroaniline (1550 g, 5.27 mmol) was dissolved in a solvent mixture of water and acetonitrile (1:5, v/v) to make a 10 L solution. Subsequently, hydrated p-toluenesulfonic acid (TsOH-H2O, 3615.0 g, 19.0 mmol) was added, and the reaction solution was cooled to 0°C. Under stirring, a 2 L aqueous solution of sodium nitrite (1085.0 g, 15.7 mmol) was added slowly dropwise, and stirring was continued for 1 hr after completion of the dropwise addition. The above solution was slowly dripped into a 2L aqueous solution of potassium iodide (KI, 3061.0 g, 18.4 mmol) and the reaction was carried out for 12 hours at room temperature. After completion of the reaction, the progress of the reaction was monitored by TLC. The reaction solution was poured into water and stirred for 30 min and the solid was collected by filtration. The filter cake was dissolved with ethyl acetate, washed sequentially with saturated sodium thiosulfate solution, saturated sodium bicarbonate solution and saturated brine, dried and concentrated to afford 1,4-diiodo-2-methoxy-5-nitrobenzene (1700 g, 4.2 mmol) in 80% yield.