Reacción #944008

Ecuación de reacción

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

N-bromosuccinimide

water

→

title compound

Rendimiento 71.0%

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

Rendimiento 71.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Temperaturacooling for 1 hour
3. 3
   Extracciónthe resulting mixture was extracted with methylene chloride
4. 4
   ExtracciónThe organic extract
5. 5
   Secadowas dried over anhydrous magnesium sulfate
6. 6
   Otrothe solvent was then removed by distillation under reduced pressure
7. 7
   Lavadoeluted with a 1:3 by volume mixture of ethyl acetate and hexane

Procedimiento

0.32 g (1.0 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) was dissolved in 10 ml of anhydrous tetrahydrofuran, and 0.18 g (1.0 mmol) of N-bromosuccinimide was added to the resulting solution, whilst ice-cooling. The mixture was then stirred, whilst ice-cooling for 1 hour and then at room temperature for a further 1 hour. At the end of this time, water was added to the mixture, and the resulting mixture was extracted with methylene chloride. The organic extract was dried over anhydrous magnesium sulfate, and 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 1:3 by volume mixture of ethyl acetate and hexane, to give 0.28 g of the title compound as a white powder (yield 70%), melting at 174-176° C.

Fuente