Sodium Carbonate → 2-(4'-Benzoylphenyl)-5-bromopyridine

Participants

Reaction Conditions

Reaction Steps

2,5-dibromopyridine (15.85 g, 66.0 mmol) was weighed into a reaction vessel in an argon stream and prepared into a solution by the addition of toluene (300 mL). 4-benzoylphenylboronic acid (18.86 g, 83.0 mmol), tetrakis(triphenylphosphine)palladium(0) (3.05 g, 2.6 mmol) and a 1.41 M aqueous sodium carbonate solution (100 mL) were added thereto, and the mixture was stirred at 90° C. for 8 hours. From the obtained reaction mixture, the solid was collected by filtration. This solid was washed with cold toluene and cold diethyl ether in this order. This solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1) and purified by silica gel column chromatography. The eluate was evaporated to dryness, and the obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2) and recrystallized several times to obtain 2-(4′-benzoylphenyl)-5-bromopyridine (3.00 g, 8.87 mmol) as a yellow solid.

Provenance & Evidence