Potassium Carbonate → HCID 19897010, compound

HRID 1196974Notes

Reaction equation

HRID 1196974 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][CH:8]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].BrBr.[F:19][C:20]([F:25])([F:24])[C:21]([NH2:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.CC(C)=O.O>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[O:16])[CH:14]([NH:23][C:21](=[O:22])[C:20]([F:25])([F:24])[F:19])[CH3:15])=[CH:11][CH:12]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24408Bromine2×HCID 67717TrifluoroacetamideHCID 19897001HCID 19897001, compound

Product 1

HCID 19897010HCID 19897010, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4'-Isoamyloxypropiophenone (100 g, 45.5 mmol) was dissolved in chloroform (100 ml), and bromine (7.63 g, 47.7 mmol) was dropwise added thereto under ice-cooling. The mixture was stirred for 3 hours, and poured into water after disappearance of bromine colour. The aqueous mixture was extracted with dichloromethane, and the extract was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated off, which gave a crude intermediate product. The product was dissolved, without purification, in acetone (100 ml) followed by the addition of trifluoroacetamide (10.2 g, 90 mmol) and anhydrous potassium carbonate (12.4 g, 90 mmol). After 1.5 hours heating under reflux, the mixture was cooled to room temperature, and the acetone was evaporated off. The residue was taken in dichloromethane, and the organic solution was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. Evaporation of the organic solvent provided a crude product which was purified by silica gel chromatography. The title compound was thus obtained. Yield: 4.44 g (29%).

Workup

  1. temperatureunder ice-cooling
  2. extractionThe aqueous mixture was extracted with dichloromethane
  3. washthe extract was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated off
  6. customwhich gave a crude intermediate product
  7. temperatureAfter 1.5 hours heating
  8. temperatureunder reflux
  9. customthe acetone was evaporated off
  10. washthe organic solution was washed with saturated aqueous sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customEvaporation of the organic solvent
  13. customprovided a crude product which
  14. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c799201673944854b5ce291c693e8e47
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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