Hydrochloric Acid → 4-(Pyridin-4-yl)benzoic acid hydrochloride

Participants

Reaction Conditions

Reaction Steps

At room temperature, 4-bromopyridine hydrochloride (11.7 g) and 4-carboxyphenylboronic acid (10.0 g) were dissolved in toluene (250 ml) and water (250 ml). To the resulting solution, tetrakis(triphenylphosphine)palladium (O) (5.00 g) and anhydrous sodium carbonate (25.4 g) were added successively, followed by refluxing under heat at 120° C. for 19 hours. After allowed to cool down to room temperature, the reaction mixture was added with ethyl acetate and water, whereby the water layer was separated. The organic layer was extracted twice with water. All the water layers so obtained were combined and to the resulting solution, concentrated hydrochloric acid was added to make it acidic, followed by washing with ethyl acetate again. The solvent was distilled off from the water layer until it decreased to 100 ml. The colorless solid so precipitated was collected by filtration and dried under reduced pressure, whereby the title compound (8.37 g, 59%) was obtained.

Provenance & Evidence