Reacción #430061

Ecuación de reacción

fluorine

fluorine

4,7-dichloroquinoline

iodine

→

2-fluoro-4,7-dichloroquinoline

Rendimiento 87.0%

Disolventes

sodium metabisulfite

—

CF2ClCFCl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted with a drying tube
2. 2
   Extracciónextracted with dichloromethane
3. 3
   OtroThe organic extracts were dried
4. 4
   Otroevaporated to an oil (0.98 g)

Procedimiento

A solution containing 4,7-dichloroquinoline (1.0 g, 5 mmol) and iodine (1.28 g, 5 mmol) in CF2ClCFCl2 (30 ml) was placed in a fluorination apparatus fitted with a drying tube filled with soda lime. Elemental fluorine (7 mmol) as a 10% mixture by volume in dry nitrogen was then passed through the stirred solution using narrow bore PTFE tubing at ca. 15 ml/min. After the fluorine had been added, the solution was poured into 10% aqueous sodium metabisulfite solution (30 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to an oil (0.98 g). GC/MS analysis showed a 34% conversion of starting material. Column chromatography on silica gel with dichloromethane as eluant gave 2-fluoro-4,7-dichloroquinoline (0.33 g, 87%) as white crystals; other data were the same as that described in the following reaction.

Fuente