2-Bromopyridine → 4-(2-Pyridyl)Benzoic Acid

Participants

Reaction Steps

2-Bromopyridine (1.26 g, 7.97 mmol), 4-carboxyphenylboronic acid (1.32 g, 7.95 mmol), and Pd(PPh3)4 (0.48 g, 0.42 mmol) were stirred at 90° overnight in CH3CN (40 mL) and 0.4 M Na2CO3 solution (40 mL, 16 mmol). After this time, the mixture was filtered hot, and the filtrate was concentrated to half-volume under reduced pressure. The remaining liquid was washed with CH2Cl2 (2×20 mL) and then acidified to pH 1 with concentrated HCl. The resulting precipitate was collected by filtration, washed with H2O, and allowed to air-dry to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.74 (m, 1H), 8.19–8.23 (m, 2H), 7.99–8.12(m, 4H), 7.47–7.52 (m, 1H); MS (ESI+) m/z 200 (M+H)+.

Provenance & Evidence