Triethylamine → N-(4-iodophenyl)-2-nitroaniline

Participants

Reaction Steps

A mixture of 2-fluoronitrobenzene (14 g, 100 mmol), 4-iodoaniline (11 g, 50 mmol) and triethylamine (14 ml, 100 mmol) was heated under reflux. After 48 h the reaction mixture was allowed to cool and ethyl acetate (300 ml) was added. The solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml). The organics were dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure to give an orange solid. Recrystalisation from ethyl acetate gave N-(4-iodophenyl)-2-nitroaniline (8.2 g, 48%) as an orange crystalline solid. deltaH (250 MHz, CDCl3) 9.39 (1H, s), 8.21 (1H, dd, J 8.5, 1.5 Hz), 7.71 (2H, dd, J 8.6, 2.0 Hz), 7.39 (1H, m), 7.24 (1H, m), 7.05 (2H, dd, J 8.6, 1.4 Hz), 6.83 (1H, m).

Provenance & Evidence