alpha-Chloro-m-nitrotoluene → 1-(Methanesulfonylmethyl)-3-nitrobenzene

HRID 1633949Notes

Reaction equation

HRID 1633949 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:12][S:13]([O-:15])=[O:14].[Na+]>CN(C=O)C>[CH3:12][S:13]([CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 12078alpha-Chloro-m-nitrotolueneHCID 2733271Sodium methanesulfinate

Product 1

HCID 179084331-(Methanesulfonylmethyl)-3-nitrobenzeneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

m-Nitrobenzyl chloride (4.21 g, 24.5 mmol) was dissolved in DMF (40 mL) and added sodium methanesulfinate (3.00 g, 29.4 mmol) and the resulting mixture was stirred at room temperature for 16 hours. After evaporation of the solvent in vacuo the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous phase was extracted with ethyl acetate (100 mL) and the combined organic phases were dried (MgSO4) and evaporated in vacuo to afford 4.45 g (84%) 1-methylsulfonylmethyl-3-nitrobenzene.

Workup

  1. customAfter evaporation of the solvent in vacuo the residue
  2. customwas partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-252cde595219478eb372eacd67fc411e
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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