Reaktion #46700

Reaktionsgleichung

3-bromobenzyl bromide

sodium methanesulfinate

→

title compound

Ausbeute 67.0%

(3-bromophenyl)methyl methyl sulfone

Ausbeute 67.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle