2,4-Dichloropyridine → 3-Chloro-4-(2-chloropyridin-4-yloxy)benzenamine

Participants

Reaction Conditions

Reaction Steps

KOtBu (1.016 g, 9.05 mmol) was added to a solution of 4-amino-2-chlorophenol (1.00 g, 6.97 mmol) in DMF (35 ml) at RT and the resultant mixture was stirred 45 min. 2,4-Dichloropyridine (1.340 g, 9.05 mmol) was then added and the reaction was stirred with heating at 90° C. overnight. The reaction was cooled to RT and diluted generously with H2O and EtOAc. The layers were separated. The aqueous was extracted with EtOAc (3×). The combined organics were washed with H2O (1×) and brine (2×), dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography (EtOAc/hexanes) to afford 3-chloro-4-(2-chloropyridin-4-yloxy)benzenamine (0.89 g, 50% yield) as a waxy yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.24 (d, J=5.7 Hz, 1H), 7.02 (d, J=8.7 Hz, 1H), 6.87-6.82 (m, 2H), 6.73-6.72 (m, 1H), 6.58-6.56 (m, 1H), 5.50 (br s, 2H); MS (ESI) m/z: 254.9 (M+H+); 256.9 (M+2+H+).

Provenance & Evidence