Tetrahydrofuran → 4-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

HRID 2298264Notes

Reaction equation

HRID 2298264 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[C:4]([CH3:16])([CH3:15])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10](SC)=[CH:9][CH:8]=1.O[O:19][S:20]([O-:22])=O.[K+].[CH2:24]1COCC1>C(O)C>[Br:1][C:2]1[C:3](=[O:17])[C:4]([CH3:16])([CH3:15])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:20]([CH3:24])(=[O:22])=[O:19])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 183859254-bromo-2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanoneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42 mg of 4-bromo-2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone was dissolved in 15 ml THF and 15 ml ethanol, to which was added 178 mg of OXONE. The mixture was stirred overnight at room temperature. Then the solvent was removed in vacuo. The resulting residue was extracted with 50 ml water and methylene chloride (50 ml×3). The organic layer was concentrated under reduced pressure and the resulting residue was subjected to column chromatographic separation (hexane/ethylacetate=2:1) to afford 45 mg of desired 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 196-196.5° C. NMR: δ1.57 (s, 6H), 3.11 (s, 3H), 8.11 (d, J=8.7 Hz, 2H), 8.40 (d, J=8.7 Hz, 2H). IR (cm−1): 2928, 1703, 1559, 1270, 1148, 1076, 847. MS (EI): 346 (m).

Workup

  1. customThen the solvent was removed in vacuo
  2. extractionThe resulting residue was extracted with 50 ml water and methylene chloride (50 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was subjected to column chromatographic separation (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-935a1bd2a70d4d71a8268c03ef4d47f7
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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