Potassium Iodide → 3-Iodo-6-methoxy-2-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

6-methoxy-2-(trifluoromethyl)pyridin-3-amine (1 g) was dissolved in H2SO4 (3 ml) and a dropwise addition of sodium nitrite (718 mg) in H2O (3 ml) was made to reaction mixture at 0° C. After 2 hour of stirring at 0° C., it was raised to room temperature. Potassium iodide (1.73 g) in H2O (3 ml) was added to the reaction mixture in a drop-wise fashion. It was heated to 60° C. for 3 hour. It was extracted with ethyl acetate, washed with sodium thiosulfate solution (Sat.), dried (MgSO4), filtered and concentrated. The flash column chromatography (SiO2, 1˜5% EtOAc in heptane) gave the title compounds (3.47 g, 67%). 1H NMR (CDCl3) δ 3.97, 6.68; 8.08; 19F NMR (CDCl3) δ 66.16; IR (liq.) 2478 (w), 2364 (w), 2230 (w), 2173 (w), 2026 (w), 1585 (s), 1471 (s), 1422 (s), 1396 (s), 1338 (s), 1280 (s), 1238 (s), 1200 (s), 1180, 1140 (s) cm−1 Anal. Calcd for C7H5F3INO: C, 27.75; H, 1.66; N, 4.62; F, 18.81. Found: C, 27.93; H, 1.80; N, 4.62.

Provenance & Evidence