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

HRID 2298293Notes

Reaction equation

HRID 2298293 reaction equation
[CH2:1]([C:3]1([CH3:19])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2].FC(F)(F)C(O[I:25](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.II>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([C:3]1([CH3:19])[C:7](=[O:8])[C:6]([I:25])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 183855812-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Product 1

HCID 183855942-ethyl-4-iodo-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneYield 135%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To 8.88 g of 2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone in 50 ml carbon tetrachloride and 50 ml chloroform, were added [bis(trifluoroacetoxy)iodo]benzene (6.82 g) and iodine (4 g). The reaction solution was stirred at room temperature for 4 hours. Then the reaction was quenched by adding saturated aqueous sodium thiosulfate until the characteristic color of iodine disappeared. The solution was extracted with 50 ml water and dichloromethane (100 ml×3). The organic layer was concentrated in vacuo and the resulting residue was purified by lo column chromatographic separation (hexane/ethylacetate=1:1) to yield 8.7 g of 2-ethyl-4-iodo-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. NMR: δ0.89 (t, J=7.5 Hz, 3H), 1.51 (s, 3H), 1.93 (q, J=7.5 Hz, 2H), 3.11 (s, 3H), 8.11 (d, J=8.7 Hz, 2H), 8.34 (d, J=8.7 Hz, 2H). IR (cm−1): 2928, 1701, 1552, 1314, 1148, 747, 551.

Workup

  1. customThen the reaction was quenched
  2. additionby adding saturated aqueous sodium thiosulfate until the characteristic color of iodine
  3. extractionThe solution was extracted with 50 ml water and dichloromethane (100 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resulting residue was purified by lo column chromatographic separation (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-22981eaf204b45babd3efb7ea0985feb
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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