Sodium Carbonate → 2-Bromo-6-phenylpyridine

Participants

Reaction Steps

A degassed solution of 2,6-dibromopyridine (4.0 g, 16.5 mmol) and phenylboronic acid (2.1 g, 16.7 mmol) in dry tetrahydrofuran (30 ml) was stirred under an atmosphere of nitrogen then sodium carbonate (3.55 g, 33.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.95 g, 5 mol %) added. This mixture was heated to reflux for 18 h. After cooling to ambient temperature, solvent was removed in vacuo, the residue dissolved in dichloromethane, washed with water and saturated brine, then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel eluting with dichloromethane gave 2-bromo-6-phenylpyridine (0.17 g) as a white solid: δH (400 MHz, CDCl3) 7.45 (4H, m), 7.60 (1H, dd, J 8 and 8), 7.70 (1H, d, J 8), 7.99 (2H, d, J 8); m/z (ES+) 233/235 (M++H).

Provenance & Evidence