3-Nitrophenol → 2-(3-nitrophenoxy)pyrazine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-nitrophenol (0.151 g, 0.733 mmol) in DMSO (5 mL) was added NaH (35 mg of a 60% dispersion, 0.88 mmol) at 0° C. under Ar atmosphere. After stirring for 30 min, 2-iodopyrazine (0.133 mg, 0.953 mmol) was added and mixture heated to 85° C. for 4 h. To the mixture was added satd. NH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography to afford (97 mg, 61% yield) 2-(3-nitrophenoxy)pyrazine as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.53 (brs, 1H), 8.38 (d, J=2.4 Hz, 1H), 8.16-8.09 (m, 3H), 7.63 (t, J=8.0 Hz, 1H), 7.57-7.54 (m, 1H); MS (ESI) m/z: 218.0 (M+H+).

Provenance & Evidence