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

HRID 2298282Notes

Reaction equation

HRID 2298282 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=[O:15])=[CH:10][CH:9]=2)[O:3]1.FC(F)(F)C(O[I:23](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.II>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[C:6](=[O:7])[C:5]([I:23])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=[O:15])=[CH:10][CH:9]=2)[O:3]1

Participants

6

Reactant 3

HCID 807IodineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 183859092,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone

Product 1

HCID 183856152,2-dimethyl-4-iodo-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanoneYield 99.9%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 6 g of 2,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone in 200 ml carbon tetrachloride and 100 ml chloroform, were added 5.15 g of [bis(trifluoroacetoxy)iodo]benzene (BTI) and 6.5 g of iodine. The reaction solution was stirred at room temperature. After 4 hours, the reaction was quenched by adding saturated aqueous sodium thiosulfate until the characteristic color of iodine disappeared. The quenched solution was extracted with water and dichloromethane (100 ml×3). The organic layer was concentrated in vacuo and the resulting crude product was recrystallized from hexane/ethylacetate to yield 4.5 g of 2,2-dimethyl-4-iodo-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone. NMR: δ1.53 (s, 6H), 2.79 (s, 3H), 7.81 (d, J=8.1 Hz, 2H), 8.38 (d, J=8.1 Hz, 2H). IR (cm−1): 2975, 2929, 1699, 1595, 1404, 1319, 1150, 969, 766, 552.

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aqueous sodium thiosulfate until the characteristic color of iodine
  3. extractionThe quenched solution was extracted with water and dichloromethane (100 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resulting crude product was recrystallized from hexane/ethylacetate

Sources & evidence

ORD record
ord-ca4c5f0899ff4783b435b6b474eedc15
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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