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

HRID 405757ノート

反応式

HRID 405757 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-8cd8fbdd76ac413b901b3c73c233cd69
出典データセット
uspto-grants-2014_06
特許番号
US08754075B2

反応ノート

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