5-chloro-4-iodo-2-nitroaniline

1635-61-6

335349-57-0

The general procedure for the synthesis of 5-chloro-4-iodo-2-nitroaniline from 2-nitro-5-chloroaniline was as follows: first, a 50 mL round-bottomed flask was prepared and purged with nitrogen to maintain an inert atmosphere. To the flask was added 5-chloro-2-nitroaniline (10 g, 57.95 mmol, 1.00 eq.), acetic acid (100 mL) and N-iodosuccinimide (NIS, 13 g, 57.78 mmol, 1.00 eq.). The reaction mixture was stirred in an oil bath at 50 °C for 3 hours. Upon completion of the reaction, the mixture was poured into 300 mL of water and the resulting solid was collected by filtration. Subsequently, the solid was washed with 200 mL of saturated sodium bicarbonate solution and three times 200 mL of water. Ultimately, 17 g (88% yield) of 5-chloro-4-iodo-2-nitroaniline was obtained as a yellow solid.