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

Participants

Reaction Conditions

Reaction Steps

A solution of sodium carbonate (830 g, 7834.20 mmol) in water (6800 mL) was added dropwise over 30 minutes to a stirred suspension of 4-boronobenzoic acid (520 g, 3133.68 mmol), 4-bromopyridine hydrochloride (622 g, 3196.35 mmol) and palladium(II) acetate (1.407 g, 6.27 mmol) in ethanol (2600 mL) and water (3600 mL) at 20° C. The reaction was stirred for 10 minutes then 3,3′,3″-phosphinidynetris(benzenesulfonic acid) trisodium salt (30% w/w solution in water) (36.8 g, 18.80 mmol) was added and the mixture was heated to 85° C. for 4 hours. The reaction mixture was cooled to 55° C. and stirred for 2 hours, then the resulting suspension was stirred at 20° C. for 16 hours. The solid was collected by filtration, washed with acetone (3×1250 mL), and dried in a vacuum oven at 60° C. to afford sodium 4-(pyridin-4-yl)benzoate (690 g, 99%) as a solid.

Provenance & Evidence