4-Aminophenol → 4-(3-Bromopyridin-2-yloxy)benzenamine

Participants

Reaction Steps

3-Bromo-2-chloropyridine (10.3 g, 53.4 mmol), 4-aminophenol (7.00 g, 64.1 mmol), cesium carbonate (34.8 g, 107 mmol), and DMSO (53 ml, 53.4 mmol) were added into a sealed tube. The tube was capped and placed in a preheated oil bath at 130° C. After 16 h, LC-MS showed mainly product. While the reaction mixture was stirring and cooling in ice-water, water was added to induce the product to precipitate out of the solution. A gray solid was obtained, washed with water, dried under vacuum at rt. MS m/z=265 [M+1]+. Calcd for C11H9BrN2O: 263.99.

Provenance & Evidence