Iodine → 3-methoxy-2-nitrobenzonitrile

Participants

Reaction Steps

3-Methoxy-2-nitrobenzaldehyde (50.2 g, 277 mmol) was dissolved in THF (300 mL) and 28% aqueous ammonium hydroxide (1000 mL) and iodine (100.7 g, 396 mmol) were slowly added. The mixture was stirred 2 h at rt, then Na2SO3 (21 g, 166 mmol) was added and the mixture stirred vigorously for 20 min. The brown-colored mixture became colorless and a precipitate formed. The solid was collected by vacuum filtration, washed well with water and dried briefly under suction to give the title compound (43 g, 87%): 1H NMR (DMSO-d6) δ: 3.94 (3H, s), 7.64 (1H, dd), 7.75-7.78 (2H, m).

Provenance & Evidence