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

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-2-chloropyridine (75.50 g, 392.3 mmol, Aldrich), 4-aminophenol (51.46 g, 471.6 mmol, TCI America) and cesium carbonate (256.80 g, 788.2 mmol, Strem) in DMSO (400 mL) in a 1 L flask and heated at 80° C. overnight. The reaction was cooled (0° C.) and diluted with water. After stirring for 30 min the mixture was filtered and the solid was partitioned between 50% EtOAc/hexane (1 L) and water (300 mL). The organic layer was washed with water (3×300 mL) and with brine (1×200 mL) then dried over Na2SO4. Filtration and concentration in vacuo gave a brown amorphous solid. MS (ESI, pos. ion) m/z: 264.9, 266.9 (M+1).

Provenance & Evidence