m-Chloroperbenzoic acid → 1-(Methylsulfinyl)-4-nitrobenzene

HRID 1391454Notes

Reaction equation

HRID 1391454 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:17]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 961094-Nitrophenyl methyl sulfide

Product 1

HCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 16.0 g (95 mmol) of 1-methylsulfanyl-4-nitro-benzene in 400 ml of DCM is mixed at room temperature with 24.6 g (100 mmol) of 3-chloroperoxybenzoic acid (about 70%). After 1 hour, the batch is diluted with DCM and washed with saturated NaHCO3 solution. The organic phase is dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 8:2). 7.6 g (41 mmol, corresponding to 43% of theory) of the product is obtained.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by chromatography (DCM/EtOH 8:2)
  6. custom7.6 g (41 mmol, corresponding to 43% of theory) of the product is obtained

Sources & evidence

ORD record
ord-2b691bbae42b4946a95260e3f266c819
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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