4-Bromoaniline → HCID 22647397, compound

Participants

Reaction Steps

In a flask outfitted with a reflux condensor, 15 (1 g, 3.2 mmol) and 4-bromoaniline (1.1 g, 6.4 mmol, 2 equiv) were melted together at 190° C. for 5 h. The reaction was cooled to room temperature and the resulting black solid was dissolved in 4:1 THF-1N NaOH soln (5 mL) stirring overnight. The reaction was diluted with EtOAc and the organic phase was washed with 1 N NaOH soln, 0.1 M HCl soln. Activated charcoal was added and the organic phase was stirred at room temperature for 0.5 h, filtered through celite and concentrated. The resulting brown solid was recrystallized from CH2Cl2 (˜4 mL) to provide the purified product as a white solid (1.2 g, 86%). 1H NMR (300 MHz, CDCl3) δ8.03 (d, J=5.9 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.23 (m, 3H), 6.42 (s, NH), 6.19 (m, 2H), 6.14 (d, J=1.9 Hz, 1H), 2.10 (s, 6H).

Provenance & Evidence