Iodine → 2-Iodo-4-methylaniline

Participants

Reaction Steps

To a stirred solution of p-toluidine (50 g, 467 mmol) in methylene chloride (250 mL) was added a solution of sodium bicarbonate (47 g, 560 mmol) in water (750 mL). Then it was added iodine (118.6 g, 467 mmol) in small portions and the mixture was stirred for 16 h at room temperature. The reaction was quenched with saturated NaHSO3 and the product was extracted with methylene chloride. The methylene chloride layer was washed with brine, dried over Na2SO4, and evaporated in vacuum to give the crude product (100 g, yield 92%). 1H NMR (300 MHz, CDCl3): δ 7.46 (s, 1H), 7.13-6.95 (d, 1H), 6.68-6.64 (d, 1H), 4.00 (br, 2H), 2.21 (s, 3H). MS: m/z 234 [M+1]+.

Provenance & Evidence