3-Hydroxypyridine → 3-(3-Nitrophenoxy)pyridine

Participants

Reaction Steps

To a solution of 3-hydroxypyridine (5.01 g, 52.7 mmol) in DMSO (60 mL) was added NaH (1.39 g, 57.9 mmol, 2.31 g of 60% suspended in oil) and stirred for 30 min at RT. To the slurry was added 1-fluoro-3-nitrobenzene (9.66 g, 68.5 mmol) and mixture was heated to 80° C. for 72 h. The mixture was poured into satd NH4Cl solution (200 mL), and extracted with EtOAc (3×125 mL). The combined organic extracts were washed with H2O (75 mL), brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography afford (4.43 g, 39% yield) pure 3-(3-nitrophenoxy)pyridine as a syrup. 1H NMR (400 MHz, Acetone-d6): δ 8.49-8.47 (m, 2H), 8.07-8.05 (m, 1H), 7.85 (t, J=2.4 Hz, 1H), 7.74 (t, J=8.4 Hz, 1H), 7.58-7.53 (m, 2H), 7.51-7.47 (m, 1H); MS (ESI) m/z: 217.0 (M+H+).

Provenance & Evidence