3-Bromobenzyl bromide → 3-Bromobenzylmethylsulfone

HRID 18422

Reaction equation

HRID 18422 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH3:10][S:11]([O-:13])=[O:12].[Na+]>CN(C)C=O>[CH3:10][S:11]([CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 2733271Sodium methanesulfinate

Product 1

HCID 27614163-BromobenzylmethylsulfoneYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. additionThe reaction mix
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed under reduced pressure
  7. customto give an oil which
  8. customwas purified by column chromatography on a 50 g isolute silica sep-pak column
  9. washeluting from 0-100% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-46b8d8503a9e4212bad9578f9f61605b
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Linked notes

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