Water → 3-(3-Nitrophenyl)pyridine

Participants

Reaction Steps

To a degassed solution of 1-iodo-3-nitrobenzene (0.35 g, 1.4 mmol) in DME (5 mL) was added Pd(PPh3)4 (0.08 g, 10% mol). After stirring for 5 min, 3-pyridylboronic acid (0.2 g, 1.65 mmol) and 2M Na2CO3 (1 mL) solution were added. After refluxing for 16 h under an Ar atmosphere, the reaction mixture was poured into H2O (15 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine, dried (Na2SO4), concentrated and purified via column chromatography to yield 3-(3-nitrophenyl)pyridine (0.22 g, 78%) as a white solid. 1H NMR (CDCl3): δ 8.94 (brs, 1H), 8.73 (brs, 1H), 8.48 (t, J=1.6 Hz, 1H), 8.32-8.29 (m, 1H), 7.98-7.93 (m, 2H), 7.72-7.68 (m, 1H), 7.48 (brs, 1H); Exact mass: 200.0, Found: 201.0 (M+1)+.

Provenance & Evidence