2-Bromo-3-pyridinol → 2-Phenyl-3-pyridinol

Participants

Reaction Steps

To a 1 liter round bottom flask equipped with a nitrogen inlet and a condenser was introduced 25 gm. (143.68 mmol) 2-bromo-3-hydroxypyridine, 19.27 gm. (156 mmol) phenylboronic acid, 5 gm (4.31 mmol) tetrakistriphenylphosphine palladium (0). The contents were dissolved in 300 ml of benzene and 100 ml of 2M aqueous sodium carbonate solution. The reaction mixture was heated under reflux for a period of 18 hours. The mixture was allowed to cool to room temperature and extracted with ethyl acetate (4×100 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was taken up in chloroform followed by treatment with ether to afford a solid precipitate. Upon filtration there was obtained 10.4 gm (42%) of 2-phenyl-3-hydroxypyridine. 1H NMR (CDCl3, 400 MHz) δ 8.22 (d, 1H), 7.71 (d, 2H), 7.51–7.40 (m, 2H), 7.22 (d, 2H), 7.15 (m, 1H) ppm. Mass spectrum APCI m/z 172 (p+1).

Provenance & Evidence