Water → 4-Cyano-2-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

Cesium fluoride (30 g, 0.22 mmol) was slurried in 150 mL dry sulfolane and concentrated via vacuum distillation at 0.5 mm Hg. After removal of 20% of the solvent, the suspension was cooled and 2-chloroisonicotinonitrile (15 g, 0.11 mmol) was added then stirred and heated at 100° C. for 20 h. It was cooled to 25° C., poured into 200 mL water and extracted with Et2O. The ether phase was washed with water, then brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica gel with CH2Cl2 to give 12.0 g of 2-fluoroisonicotinonitrile as a low-melting colorless solid. MS m/z 122. 1H NMR (CDCl3): δ 8.45 (dd, 1H), 7.47 (dd, 1H), 7.24 (m, 1H).

Provenance & Evidence