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

HRID 1186213Notes

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=O)C>[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

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester (535 mg, 3 mmole) and N-chloro-succinimide (1.22 g, 9.1 mmole) in DMF (5 ml) was heated at 50° C. overnight. The reaction mixture was cooled, partitioned between AcOEt and water, the organic layer was washed with water, dried, evaporated and the residue was purified by chromatography on silica gel using cyclohexane/AcOEt (3:1) to give the title compound (540 mg) as a white solid. MS: m/z=209.9 [M]+.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between AcOEt 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-c7bbb36bdc7d441183b155c5645fa868
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673894B2

Reaction notes

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