Chlorosuccinimide → 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester
Reaction equation
[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>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]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
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, partitioned between ethyl acetate and water, the organic layer was washed with water, dried, evaporated and the residue was purified by chromatography on silica gel using cyclohexane/ethyl acetate (3:1) as the eluent to give the title compound (540 mg) as a white solid. MS (ISP): m/z=209.9 [M]+.
Workup
- temperatureThe reaction mixture was cooled
- custompartitioned between ethyl acetate and water
- washthe organic layer was washed with water
- customdried
- customevaporated
- customthe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-46ce9ae344a14b028468bff610379aca
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785436B2
Reaction notes
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