2-Bromopyridine → 4-(2-Pyridyl)Benzoic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(dihydroxyboryl)benzoic acid (1.03 g, 6.21 mmol) and 2-bromopyridine (0.59 mL, 6.21 mmol) in ACN (20 mL) was added sodium carbonate (0.396 g, 3.74 mmol) in water (20 mL). The reaction mixture was degassed with argon and then tetrakis(triphenylphosphine)palladium (0.108 g, 0.09 mmol) was added. The reaction mixture was allowed to stir at 90° C. overnight and then filtered. The solution was concentrated to remove ACN and the aqueous solution was washed with DCM. The aqueous solution was acidified with 1N HCl and the resulting white precipitate was filtered and dried to give 4-pyridin-2-ylbenzoic acid (1.06 g, 85%). LCMS: (FA) ES+ 200.1.

Provenance & Evidence