Sulfuric Acid → Diethyl (3-chloro-2,4-difluorobenzoyl)malonate

HRID 2209982

Reaktionsgleichung

Reaktionsgleichung von HRID 2209982
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:13][C:14]1[C:15]([F:24])=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18].S(=O)(=O)(O)O>C(O)C.C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Cl:13][C:14]1[C:15]([F:24])=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:18]

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 27735383-Chloro-2,4-difluorobenzoyl chlorideHCID 5462224Magnesium

Produkt 1

HCID 22077280Diethyl (3-chloro-2,4-difluorobenzoyl)malonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3.9 g (0.16 mol) of magnesium are introduced into 8.6 ml of ethanol, and the reaction is started up using carbon tetrachloride. A solution of 23.1 g (0.144 mol) of diethyl malonate in 16.3 ml of ethanol is added dropwise at an internal temperature of 50°-60° C. in such a manner that the temperature is maintained. The mixture is subsequently stirred for one hour at 60° C. A solution of 31.3 g (0.148 mol) of 3-chloro-2,4-difluorobenzoyl chloride in 16 ml of toluene is then added dropwise at -10° to -5° C., and stirring is continued for one hour at 0° C. and subsequently overnight while the mixture comes to room temperature. The reaction mixture is poured into ice-water, acidified using 10 ml of concentrated sulphuric acid and extracted using toluene. The toluene phase is washed using saturated sodium chloride solution, and the solvent is removed in vacuo.

Aufarbeitung

  1. temperatureis maintained
  2. stirringstirring
  3. waitis continued for one hour at 0° C. and subsequently overnight while the mixture
  4. customcomes to room temperature
  5. extractionextracted
  6. washThe toluene phase is washed
  7. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ed51ee65e9d41f5ad9b0827b8619d48
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05457104

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