Sodium hydride → 2-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A 0° C. suspension of NaH (60% in mineral oil, 0.620 g, 15.5 mmol) in DMF (30 mL) was treated portion-wise with of 2-chloro-4-hydroxypyridine (1.339 g, 10.33 mmol), stirred at 0° C. for 0.5 h, slowly warmed to RT, treated with a solution of 5-chloro-2,4-difluoronitrobenzene (2 g, 10.33 mmol) in DMF (4.4 mL) and heated at 90° C. for 15 h. The mixture was cooled to RT, diluted with EtOAc, washed with 10% LiCl (3×), then brine (2×), dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 2-chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (1.415 g, 45%). 1H NMR (400 MHz, DMSO-d6): δ 8.56 (dd, 1 H), 8.35 (dd, 1 H), 7.88 (dd, 1 H), 7.32 (dd, 1 H), 7.18 (m, 1H); MS (ESI) m/z: 303.0 (M+H+).

Provenance & Evidence