Reacción #46700

Ecuación de reacción

3-bromobenzyl bromide

sodium methanesulfinate

→

title compound

Rendimiento 67.0%

(3-bromophenyl)methyl methyl sulfone

Rendimiento 67.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 16 h
2. 2
   workup.ADDITIONThe reaction mix
3. 3
   Otropartitioned between ethyl acetate and water
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried over sodium sulfate
6. 6
   Otrothe solvent removed under reduced pressure
7. 7
   Otroto give an oil which
8. 8
   Otrowas purified by column chromatography on a 50 g isolute silica sep-pak column
9. 9
   Lavadoeluting from 0-100% ethyl acetate in petroleum ether

Procedimiento

A solution of 3-bromobenzyl bromide (5.0 g, 20 mmol) in dry dimethylformamide (50 ml) at room temperature under an atmosphere of argon was treated portionwise with sodium methanesulfinate (2.0 g, 20 mmol) with stirring. The mixture was stirred at room temperature for 16 h, and then at 50° C. for 0.5 h. The reaction mix was allowed to cool to room temperature and then partitioned between ethyl acetate and water. The organic layer was separated and dried over sodium sulfate and the solvent removed under reduced pressure to give an oil which was purified by column chromatography on a 50 g isolute silica sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as an off-white solid (3.34 g, 67%).

Fuente