p-Toluenesulfonic acid → Ethyl 2,4-dichloro-5-fluorobenzoylacetate

HRID 637923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637923
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:31]=[C:30]([Cl:32])[C:29]([F:33])=[CH:28][C:14]=1[C:15]([CH:17](C(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]>O>[Cl:12][C:13]1[CH:31]=[C:30]([Cl:32])[C:29]([F:33])=[CH:28][C:14]=1[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 13326819Diethyl 2-(2,4-dichloro-5-fluorobenzoyl)malonate

Produkt 1

HCID 2774350Ethyl 2,4-dichloro-5-fluorobenzoylacetateAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.15 g of p-toluenesulphonic acid is added to an emulsion of 34.9 g of crude diethyl 2,4-dichloro-5-fluorobenzoyl-malonate (3) in 50 ml of water. The thoroughly stirred mixture is heated at the boil for 3 hours, the cooled emulsion is extracted several times with methylene chloride, the combined CH2Cl2 solutions are washed once with saturated NaCl solution and dried with Na2SO4, and the solvent is distilled off in vacuo. Fractionation of the residue in vacuo gives 21.8 g of ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate (4) of boiling point 127°-142° C./0.09 mbar.

Aufarbeitung

  1. temperatureThe thoroughly stirred mixture is heated at the boil for 3 hours
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined CH2Cl2 solutions are washed once with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. distillationthe solvent is distilled off in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-be50b00e10f5444f8d905886ad74bc9d
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559341

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