Sodium Iodide → (4-Iodopyridin-2-yl)methyl acetate

Participants

Reaction Steps

2-(((Tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine (600 mg, 2.33 mmol), dry sodium iodide (5 g) and freshly distilled acetyl chloride (0.7 mL, 9.78 mmol) in 6 mL of anhydrous acetonitrile were refluxed under nitrogen for 33 hours. Aqueous 10% K2CO3/5% NaHSO3 was added and the mixture extracted three times with chloroform. After drying (Na2SO4) and evaporation of the chloroform, flash chromatography (hexane/EtOAc 9:1) yielded 110 mg (22%) of 4-Iodo-2-methylpyridine as a white solid and 290 mg (45%) of (4-iodo-2-pyridyl)methylacetate as a white solid.

Provenance & Evidence