4-Nitroaniline → 2-Iodo-4-nitroaniline

Participants

Reaction Steps

To a solution of 4-nitroaniline (27.6 g, 0.2 mol) in 200 mL of dry acetonitrile was added a solution of ICl (31.0 g, 0.19 mol) in 50 mL of acetonitrile and the mixture was stirred at room temperature for 18 h. The reaction mixture was then poured into ethyl acetate, washed (20% aq. Na2S2O3, brine), dried (Na2SO4) and evaporated to give a brown solid. Chromatography (SiO2 /CH2Cl2 -hexane, 6:4 to 7:3) afforded the title compound (18.0 g, 36%) as a yellow solid, mp 104°-106° C.: IR (neat) 3480, 3380, 1610, 1300 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ8.38 (d, J=2.6 Hz, 1H), 7.97 (dd, J=9.0, 2.6 Hz, 1H), 6.75 (d, J=9.0 Hz, 1H), 6.73 (s, 2H).

Provenance & Evidence