Water → 5-(Chloromethyl)-2-(trifluoromethyl)pyridine

Participants

Reaction Steps

To a solution of Example 85B (2.8 g, 15.8 mmol) in 20 mL of anhydrous DMF was added POCl3 (5 mL) at 0° C. The resulting mixture was warmed to room temperature and stirred overnight. The solution was poured into 20 mL of icy water. The mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column (petroleum ether:ethyl acetate=20:1) to afford the title compound (2.1 g, 68.2%). LC-MS: m/z 300 (M+H). 1H NMR (400 MHz, CDCl3): δ 8.74 (s, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.72 (s, J=8.0 Hz, 1H), 4.66 (s, 2H).

Provenance & Evidence