p-Toluenesulfonic acid → 2,6-Difluoro-4-iodoaniline

Participants

Reaction Steps

To a solution of 2,6-difluoroaniline (5.0 g, 38.7 mmol) and p-toluenesulfonic acid (1.45 g, 7.62 mmol) in DMF (70 mL) was added dropwise N-iodosuccinimide (9.6 g, 42.7 mmol) dissolved in DMF (50 mL) at 5° C. The mixture was stirred for 2.5 hours at room temperature. The mixture was concentrated under reduced pressure, and then diluted with EtOAc and water. The organic layer was washed with saturated aqueous sodium thiosulfate and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by crystallization from EtOAc and hexane to give 2,6-difluoro-4-iodoaniline (9.12 g, 92.4%).

Provenance & Evidence