2-Chloro-5-iodopyridine (800 mg, 3.34 mmol, 1.0 eq.) was added to a solution of sodium (530 mg, 24.1 mmol, 7.2 eq.) in ethanol (15 mL) and the reaction mixture was refluxed for 12 hours. Upon completion of the reaction, ethanol was removed by distillation under reduced pressure and the residue was quenched with water. Subsequently, the reaction mixture was extracted with ethyl acetate (50 mL × 2). The organic phases were combined, washed sequentially with water (20 mL × 3) and saturated saline, and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel 100-200 mesh, eluent 2% ethyl acetate-hexane) to afford 2-ethoxy-5-iodopyridine in 60% yield.
