m-Chloroperbenzoic acid → 2,4-Dichloro-1-methanesulfinylmethoxy-benzene

HRID 390787Notes

Reaction equation

HRID 390787 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][S:11][CH3:12].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][S:11]([CH3:12])=[O:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 685778972,4-Dichloro-1-methylsulfanylmethoxy-benzene

Product 1

HCID 685778492,4-Dichloro-1-methanesulfinylmethoxy-benzeneYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of the above crude 2,4-dichloro-1-methylsulfanylmethoxy-benzene (17 g) in DCM (200 mL) was added portion wise m-CPBA (13.8 g, 79.75 mmol) during 30 min. The resulting mixture was allowed to reach room temperature and stirring was continued for 16 hrs. The organic phase was washed with water (2×100 mL), 1N NaOH until pH 6-7, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on silicagel (10 cm) using first heptane (1 L) followed by EtOAc:heptane (1:1) (1 L) and finally EtOAc as eluents. Pure fractions were collected from the pure EtOAc phase and evaporated in vacuo affording 10.1 g (69%) of 2,4-dichloro-1-methanesulfinylmethoxy-benzene as a solid.

Workup

  1. customto reach room temperature
  2. washThe organic phase was washed with water (2×100 mL), 1N NaOH until pH 6-7
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on silicagel (10 cm)
  7. customPure fractions were collected from the pure EtOAc phase
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7a2f96e1b8a347fe90d3fc257d9b83fa
Source dataset
uspto-grants-2013_02
Patent number
US08383683B2

Reaction notes

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