Hydrochloric Acid → 2-Chloro-3-hydroxy-6-iodopyridine

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Reaction Steps

Iodine (2.38 mL, 46.3 mmol) was added to a solution of 2-chloro-3-pyridinol (5.00 g, 38.6 mmol) in water (60 mL) containing potassium carbonate (18.7 g, 135 mmol). The resulting solution was allowed to stir for 2 h at room temperature. The mixture was treated with sodium thiosulfate, acidified to pH 2 using 12M aqueous HCl, and extracted with EtOAc. The organic phase was dried over MgSO4 and evaporated. Purification by flash chromatography using EtOAc/hexanes gave 2-chloro-6-iodopyridin-3-ol. 1H NMR (300 MHz, CDCl3) δ ppm 7.56 (d, J=8.2 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H). MS (ESI) m/z: Calculated; 254.9 Observed: 255.8 (M++1).

Provenance & Evidence