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

HRID 403264Notes

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-c98b58df862449de955ec0704e0bf7a5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748418B2

Reaction notes

Loading…