Water → 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester

HRID 405757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405757
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH:10]([F:12])[F:11])[N:6]=1)=[O:4].[Cl:13]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([Cl:13])=[CH:8][N:7]([CH:10]([F:12])[F:11])[N:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 57497167Methyl 1-(difluoromethyl)-1H-pyrazole-3-carboxylate

Produkt 1

HCID 574758834-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester (535 mg, 3 mmol) and N-chloro-succinimide (1.22 g, 9.1 mmol) in N,N-dimethylformamide (5 ml) was heated at 50° C. overnight. The reaction mixture was cooled, poured into water (20 ml), then extracted with ethyl acetate. The organic layer was separated, washed with water, dried over sodium sulphate, finally evaporated at reduced pressure. The yellowish crude material was purified by chromatography on silica gel using a 3:1-mixture of cyclohexane and ethyl acetate as the eluent. The 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester was obtained as a white solid (540 mg, 84% of theory). MS (ISP): m/z=209.9 [M]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customfinally evaporated at reduced pressure
  7. customThe yellowish crude material was purified by chromatography on silica gel using a 3

Quellen und Nachweise

ORD-Eintrag
ord-8cd8fbdd76ac413b901b3c73c233cd69
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754075B2

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