Reacción #944010

Ecuación de reacción

1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

polyethylene

sodium carbonate

xenon difluoride

→

title compound

Rendimiento 35.6%

5-Fluoro-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

Rendimiento 35.6%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the resulting solution at 0° C.
2. 2
   Otroto return to room temperature
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 20 hours
4. 4
   Extracciónwas then extracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium carbonate
6. 6
   Secadowith water, after which it was dried over anhydrous magnesium sulfate
7. 7
   OtroThe solvent was then removed by distillation under reduced pressure
8. 8
   Lavadoeluted with a 3:1 by volume mixture of hexane and ethyl acetate

Procedimiento

0.90 g (2.7 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) was dissolved in 10 ml of acetonitrile in a reaction vessel made of polyethylene, and 0.46 g (2.7 mmol) of xenon difluoride was added to the resulting solution at 0° C., whilst stirring. The temperature of the reaction mixture was then allowed to return to room temperature, and the mixture was stirred at room temperature for 20 hours. At the end of this time, 20 ml of a saturated aqueous solution of sodium carbonate was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium carbonate and then with water, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 3:1 by volume mixture of hexane and ethyl acetate, to give 0.32 g of the title compound as white prismatic crystals (yield 34%), melting at 140-141° C.

Fuente