Sulfuric Acid → 3-Bromo-2-(difluoromethoxy)aniline

Participants

Reaction Conditions

Reaction Steps

Into a 300-ml four-necked flask provided with a reflux condenser, a stirrer and a thermometer were fed 6.56 g of an iron powder, 0.49 g (4.7 mmol) of 95% sulfuric acid and 50 ml of water. The mixture was heated to 80° C. on an oil bath. Thereto was slowly added, at 80 to 85° C., 12.54 g (0.047 mol) of 3-bromo-2-difluoromethoxynitrobenzene. The temperature was increased and refluxing was conducted at 100° C. for 2 hours with heating. After completion of the reaction, azeotropic distillation was performed while 200 ml of water was added gradually. The distillate was subjected to extraction two times each using 30 ml of dichloromethane. The organic layer was dried over anhydrous sodium sulfate and subjected to distillation to remove the solvent and obtain 8.09 g of 3-bromo-2-difluoromethoxyaniline (yield: 72.4%, purity: 99.7%).

Provenance & Evidence