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

HRID 2381695Notes

Reaction equation

HRID 2381695 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:12]([S:14]([CH3:16])=[O:15])[Na]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CCO>[CH3:16][S:14]([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:12]

Participants

5

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 178504973HCID 178504973, compound

Product 1

HCID 2873701-(Methanesulfonylmethyl)-4-nitrobenzeneYield 120.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 4-nitrobenzyl chloride (1 g, 5.8 mmol) and TBAI (0.11 g, 0.29 mmol) in EtOH (12 mL) was added NaOSOCH3 (0.77 g, 6.38 mmol). After heating at reflux for 2 h, the mixture was cooled to room temperature, and the precipitates were collected by filtration to give 1-(methylsulfonylmethyl)-4-nitrobenzene (1.5 g).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-001f959e8f8d42dd8b0f6dcb38bf4373
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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