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

Participants

Reaction Steps

A stirred mixture of 3-nitrophenylboronic acid (2.00 g), 4-bromopyridine hydrochloride (1.56 g), bis(diphenylphosphino)butanepalladium(II) chloride (0.48 g), sodium bicarbonate (2.69 g), water (30 ml) and 1,2 dimethoxyethane (100 ml) is heated under reflux for 3 hours. The cool mixture is added to water (300 nil) and extracted with chloroform (3×150 ml), and the combined organic extracts washed with water and brine, dried (MgSO4), charcoaled and filtered. The solvent is evaporated to give a residue which is purified by flash chromatography (silica, ether) to give 1.19 g of 4-(3nitrophenyl)pyridine, mp 109-110.5° C. (from acetone/hexane).

Provenance & Evidence