Water → HCID 22633821, compound

HRID 2417140Notes

Reaction equation

HRID 2417140 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:15]=[C:16](F)[CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[C:19](=[O:22])([O-])[O-].[K+].[K+].[OH2:25]>CS(C)=O.C1(C)C=CC=CC=1>[C:2]1([O:25][C:2]2[CH:3]=[C:4]([CH:15]=[C:16]([O:22][C:19]3[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=3)[CH:17]=2)[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[O:6])[CH:3]=[CH:4][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 2758294HCID 2758294, compound

Product 1

HCID 22633821HCID 22633821, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

19.0 g (0.077 mole) of 3,5-difluoro-4′-methoxybenzophenone are dissolved under argon in a mixture of 200 ml of dimethyl sulfoxide and 200 ml of toluene. 28.56 g (0.207 mole) of finely powdered potassium carbonate are added to this solution. The solution is stirred under reflux for 4 hours, the water formed being removed in a water separator. The toluene is then completely distilled off and the reaction mixture is stirred for a further 3 hours at 150° C. A further 28.56 g (0.207 mole) of finely powdered potassium carbonate and 50 ml of toluene are added. The mixture is heated under reflux and the toluene is distilled off. The solution is stirred for a further 4 hours at 150° C. After cooling, the solution is poured onto ice. The solution is neutralised by adding HCl solution (10%). Extraction with diethyl ether is performed several times. The combined organic phases are washed with saturated sodium chloride solution. The product is dried over magnesium, sulfate and the solvent is removed in vacuo. The crude product is chromatographed on silica gel (silica gel 60, 0.040-0.063 mm, Merck) using n-hexane/ethyl acetate (19:1). 14.90 g (49%) of a pale yellow oil are obtained.

Workup

  1. temperatureunder reflux for 4 hours
  2. custombeing removed in a water separator
  3. distillationThe toluene is then completely distilled off
  4. stirringthe reaction mixture is stirred for a further 3 hours at 150° C
  5. additionA further 28.56 g (0.207 mole) of finely powdered potassium carbonate and 50 ml of toluene are added
  6. temperatureThe mixture is heated
  7. temperatureunder reflux
  8. distillationthe toluene is distilled off
  9. stirringThe solution is stirred for a further 4 hours at 150° C
  10. temperatureAfter cooling
  11. additionthe solution is poured onto ice
  12. additionby adding HCl solution (10%)
  13. extractionExtraction with diethyl ether
  14. washThe combined organic phases are washed with saturated sodium chloride solution
  15. dry with materialThe product is dried over magnesium, sulfate
  16. customthe solvent is removed in vacuo
  17. customThe crude product is chromatographed on silica gel (silica gel 60, 0.040-0.063 mm, Merck)

Sources & evidence

ORD record
ord-f7f903e4302845209ebb6ccd45eed7f9
Source dataset
uspto-grants-2004_11
Patent number
US06825312B2

Reaction notes

Loading…