3-Nitrophenylboronic Acid → 4-(3-Nitrophenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromopyridine hydrochloride (5.25 g) and tetrakis(triphenylphosphine)palladium(0) (0.93 g) in toluene (50 ml) was added 3M aqueous solution of sodium bicarbonate (27 ml) and a solution of dihydroxy(3-nitrophenyl)borane (5.0 g) in methanol (12 ml). The mixture was stirred at 80° C. for 1 hour and cooled. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (1%-2% methanol in chloroform) to give 4-(3-nitrophenyl)pyridine (3.46 g).

Provenance & Evidence