Sodium Carbonate → 5-Bromo-2-phenylpyridine

Participants

Reaction Conditions

Reaction Steps

2,5-dibromopyridine (7.11 g, 30 mmol), toluene (130 mL), phenylboronic acid (4.57 g, 37.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) were weighed into a reaction vessel, and the reaction mixture was dissolved with stirring at 50° C. in a nitrogen stream. To this solution, a 2 M aqueous sodium carbonate solution (30 mL) was added, and the mixture was stirred at 80° C. for 6 hours. The organic layer of the obtained reaction solution was collected and washed with an aqueous sodium carbonate solution and a saturated brine. The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. This residue was purified by silica gel column chromatography (hexane/toluene). The eluate was evaporated to obtain 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol).

Provenance & Evidence