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

Participants

Reaction Steps

1-fluoro-3-nitrobenzene (1 g, 7 mmol, 1 eq), 3-hydroxypyridine (674 mg, 7.09 mmol, 1.00 eq), K2CO3 (1.18 g, 8.54 mmol, 1.20 eq) and DMF (10 mL) were added to a microwave vial and microwaved at 200° C. for 30 minutes. The reaction was filtered and concentrated on silica gel (5 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 1.1 g (72%) of the title compound as a brown oil: 1H NMR (400 MHz, DMSO-d6) 8.49 (d, J=2.8 Hz, 1H), 8.46 (d, J=4.6 Hz, 1H), 8.02 (dd, J=8.2, 2.0 Hz, 1H), 7.78 (t, J=2.3 Hz, 1H), 7.70 (t, J=8.2 Hz, 1H), 7.60 (m, 1H), 7.54 (dd, J=8.3, 2.4 Hz, 1H), 7.49 (dd, J=8.4, 4.6 Hz, 1H); ES-MS [M+1]+: 217.2

Provenance & Evidence