Hydrochloric Acid → 5-Chloro-2-phenylbenzofuran-7-carboxylic acid

HRID 1761904

Reaktionsgleichung

Reaktionsgleichung von HRID 1761904
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=O)[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].Br[CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C(OC)=O.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[C:5]2[O:12][C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 13146779Methyl 5-chloro-3-formyl-2-hydroxybenzoate

Produkt 1

HCID 142297055-Chloro-2-phenylbenzofuran-7-carboxylic acidAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3.0 g of methyl 5-chloro-3-formyl-2-hydroxybenzoate, 3.44 g of methyl α-bromophenylacetate, 8.28 g of potassium carbonate and 50 ml of dimethylformamide is heated at 70°-80° C. for 15 minutes and further heated at 100° C. for 10 minutes. After cooling, water is added to the mixture, and the aqueous mixture is acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is dissolved in 50 ml of ethanol, and 4.5 g of potassium hydroxide are added to the solution. The mixture is refluxed for 1 hour and then evaporated to remove solvent. Water is added to the residue, and the aqueous mixture is acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract is dried and evaporated to remove solvent. 150 ml of xylene and 30 mg of p-toluenesulfonic acid are added to the residue and the mixture is refluxed for 1 hour. The reaction mixture is evaporated to remove solvent and the residue is dissolved in ethyl acetate. The solution is washed, dried and evaporated to remove solvent. The residue is crystallized from isopropyl ether to give 2.32 g of 5-chloro-2-phenylbenzofuran-7-carboxylic acid.

Aufarbeitung

  1. temperatureis heated at 70°-80° C. for 15 minutes
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with an aqueous saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. dissolutionThe residue is dissolved in 50 ml of ethanol
  9. addition4.5 g of potassium hydroxide are added to the solution
  10. temperatureThe mixture is refluxed for 1 hour
  11. customevaporated
  12. customto remove solvent
  13. additionWater is added to the residue
  14. extractionextracted with ethyl acetate
  15. customThe extract is dried
  16. customevaporated
  17. customto remove solvent
  18. addition150 ml of xylene and 30 mg of p-toluenesulfonic acid are added to the residue
  19. temperaturethe mixture is refluxed for 1 hour
  20. customThe reaction mixture is evaporated
  21. customto remove solvent
  22. dissolutionthe residue is dissolved in ethyl acetate
  23. washThe solution is washed
  24. customdried
  25. customevaporated
  26. customto remove solvent
  27. customThe residue is crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-49ce5ea3953d4a788a763a4259ab44f7
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04829067

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