Dimethylformamide → 1-Bromo-4-((methylsulfonyl)methyl)benzene

HRID 874461Notes

Reaction equation

HRID 874461 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.CN(C)C=O.[CH3:15][S:16]([O-:18])=[O:17].[Na+]>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 685274-Bromobenzyl bromideHCID 2733271Sodium methanesulfinate

Product 1

HCID 27614151-Bromo-4-((methylsulfonyl)methyl)benzeneYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A 250 mL round-bottomed flask was charged with 4-bromobenzyl bromide (5 g, 20 mmol) and N,N-dimethylformamide (10.81 mL). Sodium methanesulfinate (3.06 g, 30 mmol) was added. The reaction mixture was stirred at 65° C. for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with water. The resulting suspension was stirred for 10 minutes and filtered. The solid was rinsed with water and dried under house vacuum over the weekend to provide 4.75 g (95%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. stirringThe resulting suspension was stirred for 10 minutes
  3. filtrationfiltered
  4. washThe solid was rinsed with water
  5. customdried under house vacuum over the weekend

Sources & evidence

ORD record
ord-aadcf15d758546bbb4417297c61dfe81
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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