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

Participants

Reaction Steps

To 3-bromopyridine (8.53 g, 54 mmol) in ethyleneglycol dimethylether (180 ml) is added 3-nitrophenylboronic acid (10 g, 59.95 mmol), aqueous potassium carbonate (90 ml, 2M) and tetrakis(triphenylphosphine)palladium (0.5 g, 0.43 mmol). The mixture is refluxed gently in a nitrogen atmosphere overnight. The cooled reaction mixture is filtered and water (600 ml) is added to the filtrate. The precipitate is filtered off and washed with water. This crude product is dissolved in hot water (400 ml) with addition of hydrochloric acid (25 ml, 4 M). The mixture is filtered while still hot. The filtrate is cooled in an ice bath and pure 3-(3-pyridyl)-nitrobenzene is precipitated by addition of 12 M NaOH. Yield 9.14 g (85%).

Provenance & Evidence