Sodium Carbonate → 5-Bromo-2-phenylpyridine

Participants

Reaction Conditions

Reaction Steps

2,5-dibromopyridine (7.11 g, 30 mmol), toluene (130 mL), phenylboric acid (4.57 g, 37.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) were weighed and placed into a reactor. A reactant was dissolved under a nitrogen stream while stirring at 50° C. To this, a 2 M sodium carbonate aqueous solution (30 mL) was added, and stirring was performed at 80° C. for 6 hours. An organic layer of the obtained reaction solution was collected, and washed with a sodium carbonate aqueous solution and a saturated brine. The organic layer was dried with sodium sulfate, filtered, and then distilled off. This residue was purified using silica gel column chromatography (hexane/toluene) to distill off the solvent, and 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol) was obtained.

Provenance & Evidence