2-Bromopyridine → 2-(o-Tolyl)pyridine

Participants

Reaction Steps

To a degassed solution of 2-bromopyridine (1.9 mL, 20 mmol) in ethylene glycol dimethyl ether (60 mL) under argon, tetrakis(triphenylphosphane) palladium (o) (700 mg, 0.6 mmol) was added. After stirring for 10 min, 2-methylphenyl boronic acid (2.9 g, 22 mmol) was added, followed by sodium bicarbonate solution (5.04 g, 60 mmol in 60 mL water). The mixture was heated to reflux (~85° C.) and stirred overnight. After cooling to room temperature, the solvent was evaporated, the residue was partitioned between water and ether, and the aqueous layer was extracted twice with ether. The combined organic layers were dried (Na2SO4), and the solvent was evaporated to give a black oil. This oil was distilled at <1 Torr at ~95° C. to give title compound (2.75 g, 82% yield) as a clear oil. ##STR91##

Provenance & Evidence