2-Fluorobenzoyl chloride → HCID 178496930, Verbindung

HRID 1248342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248342
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:11]=2[CH:10]=1)=[O:8].[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>C(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([OH:17])[C:15]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[F:19])=[CH:16][C:11]=2[CH:10]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Produkt 1

HCID 178496930HCID 178496930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

26.6 g of finely pulverised aluminium chloride are suspended in 60 ml of methylene chloride. While stirring and while cooling slightly, 9.61 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester, dissolved in a small amount of methylene chloride, are added dropwise at room temperature. After stirring for 30 minutes at room temperature, 15.85 g of o-fluorobenzoyl chloride are added dropwise thereto and the resulting reaction mixture is heated at reflux for 4 hours. After cooling, the reaction mixture is poured onto ice and extracted thoroughly with methylene chloride. The combined organic phases are washed with water, dried over magnesium sulphate and concentrated by evaporation. The yellow oily residue (20 g) is chromatographed over 400 g of silica gel with methylene chloride. Fractions 7-16 (50 ml fractions) are combined and concentrated. The residue is crystallised from ether/petroleum ether. 4-(o-fluorobenzoyl)-5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester is obtained in the form of yellow crystals having a melting point of 59°-61°.

Aufarbeitung

  1. temperaturewhile cooling slightly
  2. additionare added dropwise at room temperature
  3. stirringAfter stirring for 30 minutes at room temperature
  4. customthe resulting reaction mixture
  5. temperatureis heated
  6. temperatureat reflux for 4 hours
  7. temperatureAfter cooling
  8. additionthe reaction mixture is poured onto ice
  9. extractionextracted thoroughly with methylene chloride
  10. washThe combined organic phases are washed with water
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated by evaporation
  13. customThe yellow oily residue (20 g) is chromatographed over 400 g of silica gel with methylene chloride
  14. concentrationconcentrated
  15. customThe residue is crystallised from ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-af2642a4ce534b6ca7df4ba3b76a188e
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04523030

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