5-Chloro-2-nitroaniline → 5-Chloro-4-iodo-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-2-nitroaniline (20.1 g, 116 mmol) and N-iodosuccinimide (26.2 g, 116 mmol) in 260 mL of acetic acid was heated at 55° C. for 16 h and then cooled in an ice-bath. The resulting yellow solid was collected by filtration and rinsed with acetic acid, water, aqueous NaHCO3 and water, and let stand in air for 2 h to provide 5-chloro-4-iodo-2-nitroaniline 1-5 as a yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 7.23 (s, 1H), 8.32 (s, 1H), 7.57 (s, 2H).

Provenance & Evidence