4-Nitrobenzyl bromide → 1-(Methanesulfonylmethyl)-4-nitrobenzene

HRID 874436Notes

Reaction equation

HRID 874436 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][S:13]([O-:15])=[O:14].[Na+]>CN(C)C=O.O>[CH3:12][S:13]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 2733271Sodium methanesulfinate

Product 1

HCID 2873701-(Methanesulfonylmethyl)-4-nitrobenzeneYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-nitrobenzyl bromide (10.0 g, 46.4 mmol) in dimethylformamide (25 mL) was added sodium methanesulfinate (7.10 g, 69.6 mmol). The reaction mixture was stirred at 65° C. for 1 hour. The reaction mixture was cooled to ambient temperature, diluted with water, stirred for 10 minutes and filtered to give the title compound (9.27 g, 93%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. stirringstirred for 10 minutes
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cf7ee0167c11479b925755ddf1bd625e
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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