1-Fluoro-3-nitrobenzene → 3-Chloro-5-(3-nitrophenoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-chloro-3-hydroxypyridine (0.45 g, 3.5 mmol) and NaH (0.15 g of 60% dispersion, 3.83 mmol) in DMSO (10 mL) was stirred at RT for 30 min and then treated with 1-fluoro-3-nitrobenzene (0.69 g, 4.9 mmol). The mixture was heated at 120° C. for 24 h, cooled to RT, quenched with satd. NH4Cl (50 mL), and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified via column chromatography using to yield 3-chloro-5-(3-nitrophenoxy)pyridine (0.2 g, 23% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): □ 8.46 (d, J=−2.0 Hz, 1H), 8.35 (d, J=2.0 Hz, 1H), 8.09 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.89 (t, J=2.0 Hz, 1H), 7.60 (t, J=8.0 Hz, 1H), 7.41-7.39 (m, 2H); MS (ESI) m/z: 251.0 (M+H+).

Provenance & Evidence