Hydrochloric Acid → 4-Iodo-3-nitroanisole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxy-2-nitroaniline (20 g, 0.12 mol) and concentrated HCl (30 mL) in water (30 mL) is refluxed for 15 min. The reaction mixture is cooled down to 0° C. in an ice bath. A solution of sodium nitrite (10 g, 0.14 mol) in water (30 mL) is added dropwise over 30 min. The resulting solution is stirred at 0° C. for 30 min then added dropwise to a cold solution of potassium iodide (30 g, 0.18 mol) in water (30 mL). The reaction mixture is heated to reflux for 2 h, cooled down to room temperature and diluted with EtOH (200 mL). The organic phase is washed with 3 N (100 mL) then water and dried over Na2SO4. The solvent is removed under reduced pressure and the crude product is purified by column chromatography using hexane as eluent affording 16 g (88%) of the title compound as a yellow crystalline 1H NMR (DMSO-d6, 400 MHz) δ 7.93-7.91 (m, 1H), 7.54 (s, 1H), 7.04-7.01 (m, 1H), 3.82 (s, 3H).

Provenance & Evidence