Acetic Acid → 4-bromo-2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone

HRID 2298263Notes

Reaction equation

HRID 2298263 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=2)[O:3]1.C(O)(=O)C.[Br:21]Br>C(Cl)(Cl)(Cl)Cl>[Br:21][C:5]1[C:6](=[O:7])[C:2]([CH3:16])([CH3:1])[O:3][C:4]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 183856882,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone

Product 1

HCID 183859254-bromo-2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone (45 mg) in 20 ml carbon tetrachloride, were added acetic acid (0.5 ml) and bromine (0.1 ml). The reaction solution was stirred at room temperature for one hour. Then the reaction was quenched by adding 20 ml of saturated aqueous sodium thiosulfate solution to the reaction solution. After removing the carbon tetrachloride in vacuo, the resulting aqueous layer was extracted with dichloromethane (50 ml×3) and the organic layer was then washed with water (50 ml×1). The organic layer was concentrated in vacuo and the resulting residue was chromatographed (hexane/ethylacetate=2:1) to yield 69 mg of 4-bromo-2,2-dimethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone as a solid. NMR: δ1.52 (s, 6H), 2.55 (s, 3H), 7.33 (d, J=9.3 Hz, 2H), 8.15 (d, J=9.0 Hz, 2H); IR (cm−1): 1704, 1594, 1574, 1486, 1348, 1184, 1069.

Workup

  1. customThen the reaction was quenched
  2. additionby adding 20 ml of saturated aqueous sodium thiosulfate solution to the reaction solution
  3. customAfter removing the carbon tetrachloride in vacuo
  4. extractionthe resulting aqueous layer was extracted with dichloromethane (50 ml×3)
  5. washthe organic layer was then washed with water (50 ml×1)
  6. concentrationThe organic layer was concentrated in vacuo
  7. customthe resulting residue was chromatographed (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-fa90c2a6d31f458e86da38456d64430e
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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