Reacción #79041

Ecuación de reacción

6-chloro-2-cyano-3-nitropyridine

KF

water

→

2-cyano-6-fluoro-3-nitropyridine

Disolventes

MeCN

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated
2. 2
   Temperaturaunder reflux
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe extract is washed with water
5. 5
   Otrothe residue is chromatographed on silica gel
6. 6
   Lavadoeluting with EtOAc/petroleum ether (3:7)
7. 7
   Otroto give
8. 8
   Otroafter removal of the solvent under reduced pressure 2-cyano-6-fluoro-3-nitropyridine (7.2 g, 79%)

Procedimiento

A mixture of 6-chloro-2-cyano-3-nitropyridine [Colbry, N. L.; Elslager, E. F. ; Werbel, L. M.; J. Het. Chem., 1984, 21, 1521-1525] (10.0 g, 0.054 mol) and KF (9.48 g, 0.163 mol) in MeCN (200 mL) is heated under reflux with stirring for 18 h, then poured into water and extracted with EtOAc. The extract is washed with water and worked up, and the residue is chromatographed on silica gel, eluting with EtOAc/petroleum ether (3:7), to give after removal of the solvent under reduced pressure 2-cyano-6-fluoro-3-nitropyridine (7.2 g, 79%). 1H NMR (CDCl3) δ 8.79 (1H, dd, J=9.0, 6.0 Hz), 7.48 (1H, dd, J=9.0, 3.0 Hz).

Fuente