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Sulfuric Acid → Diethyl (2,3-dichloro-4,5-difluorobenzoyl)propanedioate

HRID 2232632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2232632
[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:22]([Cl:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(O)C.C(Cl)(Cl)(Cl)Cl>[Cl:13][C:14]1[C:22]([Cl:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 10999320Benzoyl chloride, 2,3-dichloro-4,5-difluoro-

Produkt 1

HCID 14071801Diethyl (2,3-dichloro-4,5-difluorobenzoyl)propanedioateAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
2×
HCID 1140TolueneLösungsmittel2×
HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Magnesium turnings (0.77 g) and carbon tetrachloride (0.4 ml) was added to absolute ethanol (5.3 ml). To the stirring suspension was added a solution of diethyl malonate (4.89 g) and absolute ethanol (8.5 ml) in toluene (21.3 ml) dropwise during 40 minutes at 20° to 40° C. The mixture was stirred at 50° to 60° C. for 2 hours, and then cooled in an acetone-dry ice bath. A solution of 2,3-dichloro-4,5-difluorobenzoyl chloride (6.00 g) in anhydrous toluene (7.1 ml) was added dropwise to the resulting solution at -18° to -13° C. during 10 minutes. The mixture was warmed gradually to room temperature during 2 hours and then mixed with ice water (17 ml) containing concentrated sulfuric acid (1.1 ml). The resulting organic layer was collected and the water layer was extracted with toluene. The combined organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated to give the title compound (9.68 g) as pale yellow oil.

Aufarbeitung

  1. temperaturecooled in an acetone-dry ice bath
  2. customThe resulting organic layer was collected
  3. extractionthe water layer was extracted with toluene
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bf7c0540b87742ffbc083bbae5ab2b3d
Quelldatensatz
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04788320

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