Disodium disulfite → 1-(Cyclopropanesulfinyl)-4-nitrobenzene

HRID 1391470Notes

Reaction equation

HRID 1391470 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.I(O)(=O)(=O)=[O:15].S(OS([O-])=O)([O-])=O.[Na+].[Na+]>C(#N)C.C(Cl)Cl.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH:1]1([S:4]([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 24346Disodium disulfiteHCID 65185Metaperiodic acidHCID 59252683Cyclopropyl(4-nitrophenyl)sulfane

Product 1

HCID 595508341-(Cyclopropanesulfinyl)-4-nitrobenzeneYield 71.3%

Reagents, catalysts & solvents 3

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

350 mg of 1-(cyclopropylsulfanyl)-4-nitrobenzene is dissolved in 5 ml of acetonitrile and mixed with 10 mg of iron(III)-chloride hexahydrate. After 10 minutes of stirring at room temperature, 450 mg of periodic acid is added thereto while being cooled. The mixture is stirred for 30 minutes at room temperature, cooled in an ice bath and mixed drop by drop with semi-saturated sodium disulfite solution. It is diluted with methylene chloride, washed with water, sodium bicarbonate solution and saturated sodium chloride solution, and concentrated by evaporation. After purification by flash chromatography, 270 mg of (RS)-1-(cyclopropylsulfinyl)-4-nitrobenzene is obtained.

Workup

  1. temperaturewhile being cooled
  2. stirringThe mixture is stirred for 30 minutes at room temperature
  3. temperaturecooled in an ice bath
  4. washwashed with water, sodium bicarbonate solution and saturated sodium chloride solution
  5. concentrationconcentrated by evaporation
  6. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-d34860490aac4e37bbb30de6dc0dbbec
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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