Ethyl bromoacetate → ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

HRID 238674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238674
[Cl:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:6]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1785061975-chloro-3-(trifluoromethyl)-1H-pyrazole2×

Produkt 1

HCID 66016896ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 5-chloro-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Example 10, Step C) (2.1 g, 12.3 mmol) and potassium carbonate (3.6 g, 26.0 mmol) in 20 mL of N,N-dimethylformamide was added ethyl bromoacetate (2.1 mL, 18.8 mmol), and the resulting mixture was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate, washed with water, and dried (MgSO4). The reaction mixture was concentrated in vacuo and further purified by medium-pressure liquid chromatography using 0-50% of ethyl acetate in hexanes as eluant to give 940 mg of the title compound as an oil.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customfurther purified by medium-pressure liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be079ffc1c7142658e3b6a85428947e1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642634B2

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