Acetic Acid → 4-Bromo-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2h)-one

HRID 2298316Notes

Reaction equation

HRID 2298316 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.C(O)(=O)C.[Br:22]Br>C(Cl)(Cl)(Cl)Cl>[Br:22][C:5]1[C:6](=[O:7])[C:2]([CH3:17])([CH3:1])[O:3][C:4]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 183859092,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone

Product 1

HCID 183859494-Bromo-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2h)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone (135 mg) in 25 ml of CCl4, were added 1 ml acetic acid and 0.1 ml bromine. The reaction mixture was stirred at room temperature for 2.5 hr. Then the reaction was quenched by adding 10 ml of saturated aqueous sodium thiosulfate. The volatile materials were removed in vacuo, which was followed by extraction with dichloromethane (50 ml×3). The organic layer was dried over anhydrous magnesium sulfate and the magnesium sulfate was filtered off. The filtrate was concentrated in vacuo and the crude product was purified by column chromatography (hexane/ethylacetate=1:1) to give 68 mg of 4-bromo-2,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone. mp: 117-118° C. NMR: δ1.55 (s, 6H), 2.79 (s, 3H), 7.81 (d, J=8.2 Hz, 2H), 8.38 (d, J=8.2 Hz, 2H). IR (cm−1): 1706, 1601,1555, 1191, 1052.

Workup

  1. customThen the reaction was quenched
  2. additionby adding 10 ml of saturated aqueous sodium thiosulfate
  3. customThe volatile materials were removed in vacuo, which
  4. extractionwas followed by extraction with dichloromethane (50 ml×3)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe magnesium sulfate was filtered off
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe crude product was purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-134d7d5d52404827af341430238a18fb
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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