N-Iodosuccinimide → 2-Iodo-4-[(methylsulfonyl)methyl]benzenamine

Participants

Reaction Steps

To a solution of Example 3b (1.12 g, 6.03 mmol) in dimethylformamide (60.3 mL) was added N-iodosuccinimide (1.49 g, 6.63 mmol). The reaction mixture was stirred at ambient temperature for 90 minutes. The reaction mixture was quenched with 10% sodium thiosulfate and saturated aqueous sodium bicarbonate, and extracted with ethyl acetate three times. The combined organic layers were washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated. Water was added to the residue, and the mixture was stirred at ambient temperature for 10 minutes and filtered to give the title compound (1.55 g, 83%).

Provenance & Evidence