Dichloromethane → 1-(Ethylsulfinyl)-4-nitrobenzene

HRID 1027856Notes

Reaction equation

HRID 1027856 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].I(O)(=O)(=O)=[O:14].C(Cl)Cl.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.[Fe](Cl)(Cl)Cl>[CH2:1]([S:3]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:14])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 61475Sodium Thiosulfate PentahydrateHCID 65185Metaperiodic acidHCID 123213391-(Ethylsulfanyl)-4-nitrobenzene

Product 1

HCID 2791461-(Ethylsulfinyl)-4-nitrobenzeneYield 68%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6342AcetonitrileSolvent

Procedure

428 mg (2.64 mmol) of iron(III) chloride was added to a mixture of 16.86 g (92.02 mmol) of 1-ethylsulfanyl-4-nitrobenzene in 75 ml acetonitrile and it was stirred for 10 minutes at room temperature. Then 22.44 g (98.44 mmol) of periodic acid was added in portions, so that the temperature did not exceed 30° C. The mixture was stirred for 50 minutes and was then added, with stirring, to a mixture of 170 ml DCM, 500 ml ice water and 100 g sodium thiosulfate pentahydrate. It was extracted with DCM (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was recrystallized from ethyl acetate/hexane. 12.49 g (62.69 mmol; yield: 68%) of the product was obtained.

Workup

  1. customdid not exceed 30° C
  2. stirringThe mixture was stirred for 50 minutes
  3. additionwas then added
  4. extractionIt was extracted with DCM (2×)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe residue obtained
  9. customwas recrystallized from ethyl acetate/hexane
  10. custom12.49 g (62.69 mmol; yield: 68%) of the product was obtained

Sources & evidence

ORD record
ord-54a575e599ac45c5ae1f9cc7cb9a8cfb
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

Loading…