Iodine → 2-ethyl-4-iodo-2-methyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone

HRID 2298295Notes

Reaction equation

HRID 2298295 reaction equation
[CH2:1]([C:3]1([CH3:18])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2].FC(F)(F)C(O[I:24](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([C:3]1([CH3:18])[C:7](=[O:8])[C:6]([I:24])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 807Iodine2×HCID 24477Sodium ThiosulfateHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 183856262-ethyl-2-methyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone

Product 1

HCID 183860342-ethyl-4-iodo-2-methyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanoneYield 162.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

8.2 g of 2-ethyl-2-methyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone in 200 ml carbon tetrachloride and 200 ml chloroform was mixed with 6.8 g of [bis(trifluoroacetoxy)iodo]benzene (BTI) and 4.1 g of iodine. The mixture was stirred at room temperature for 6 hours, followed by quenching the reaction by adding saturated aqueous sodium thiosulfate until the characteristic color of iodine disappeared. The quenched solution was extracted with 300 ml water and dichloromethane (200 ml×3). The organic layer was concentrated in vacuo and the resulting residue was purified by column chromatography (hexane/ethylacetate=1:1) to give 10.0 g of 2-ethyl-4-iodo-2-methyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone. NMR: δ0.89 (t, J=7.5 Hz, 3H), 1.51 (s, 3H), 1.93 (m, 2H), 2.73 (s, 3H), 7.81 (d, J=8.7 Hz, 2H), 8.38 (d, J=8.7 Hz, 2H).

Workup

  1. customby quenching
  2. customthe reaction
  3. extractionThe quenched solution was extracted with 300 ml water and dichloromethane (200 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resulting residue was purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-02be43986f774175bd232f9a19373fdb
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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