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

HRID 1449839

Reaktionsgleichung

Reaktionsgleichung von HRID 1449839
[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 initially introduced into 8.6 ml of ethanol and the reaction is started with 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. such that this temperature is maintained. The mixture is then subsequently stirred at 60° C. for one hour. Thereafter, a solution of 31.3 g (0.148 mol) of 3-chloro-2,4-difluorobenzoyl chloride in 16 ml of toluene is added dropwise at -10° to -5° C. and the mixture is subsequently stirred at 0° C. for one hour and then overnight, while warming to room temperature. The reaction mixture is poured onto ice-water, acidified with 10 ml of concentrated sulphuric acid and extracted with toluene. The extract is washed with saturated sodium chloride solution and the solvent is removed in vacuo.

Aufarbeitung

  1. temperatureis maintained
  2. stirringthe mixture is subsequently stirred at 0° C. for one hour
  3. temperatureovernight, while warming to room temperature
  4. additionThe reaction mixture is poured onto ice-water
  5. extractionextracted with toluene
  6. washThe extract is washed with saturated sodium chloride solution
  7. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-af8b5f66174c455397287bf8f4c8131d
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599980

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