m-Chloroperbenzoic acid → HCID 21876260, compound

HRID 724174Notes

Reaction equation

HRID 724174 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[S:12]([CH3:14])=[O:13].ClC1C=C(C=CC=1)C(OO)=[O:20].C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[S:12]([CH3:14])(=[O:20])=[O:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 21876463HCID 21876463, compound

Product 1

HCID 21876260HCID 21876260, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,5-dichloro-2-(methylsulfinyl)-4-nitrobenzene (1.0 g, 3.9 mmol) in dichloromethane (50 ml) was added 3-Chloroperoxybenzoic acid (1.7 g, 9.8 mmol). The mixture was stirred under nitrogen at room temperature for 3 h. The mixture was added saturated aqueous NaHCO3 (20 ml) and extracted with dichloromethane (50 ml). The organic layer was washed with brine (50 ml), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (2:1) to give 1 g (100%) of the title compound as white solids.

Workup

  1. extractionextracted with dichloromethane (50 ml)
  2. washThe organic layer was washed with brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-75be9f552dc94aea99d390035598e6a7
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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