Phosphorus oxychloride → 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (53 g, 0.18 mmol) and POCl3 (67 mL, 0.73 mmol) in DMF (50 mL) was heated to 110° C. for 4 h. The reaction mixture was cooled to room temperature and then slowly poured into an ice/water bath. The brown solid was filtered and washed with water. It was then dissolved in DCM, washed with an aqueous saturated solution of sodium thiosulfate (2×), dried over sodium sulfate, and concentrated to dryness to afford 47 g of 2-chloro-5-iodo-3-(trifluoromethyl)pyridine as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.79 (d, 1H), 8.29 (d, 1H).

Provenance & Evidence