Sodium Carbonate → Sodium 4-(pyridin-4-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 4-bromopyridine hydrochloride (0.770 g, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and the mixture was purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added and the reaction mixture heated to 90° C. for 22 hours. The precipitated sodium salt was filtered, washed with acetonitrile and then dried in vacuo at 50° C. overnight to give the title compound (0.162 g, 18%) as a grey solid.

Provenance & Evidence