Phosphorus oxychloride → 3-Bromo-4-chlorothieno(3,2-c)pyridine

Participants

Reaction Steps

A stirred mixture of 3-bromo-5H-thieno[3,2-c]pyridine-4-one (1.16 g, 5.04 mmol) and phosphorus oxychloride (20 ml) was heated to reflux for 4 h. The reaction was then allowed to cool to room temperature and the phosphorus oxychloride removed in vacuo. The residue was dissolved in DCM (25 ml) and washed with distilled water (2×25 ml) followed by saturated sodium hydrogen carbonate solution (25 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was then subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 5:1, Rf 0.5) to afford the title compound as a yellow solid (398 mg, 32%).

Provenance & Evidence