Chlorine → 1-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethyl-4-chloropyrazole

HRID 580266Notes

Reaction equation

HRID 580266 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][C:3]=1[N:14]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[N:15]1.[Cl:21]Cl>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][C:3]=1[N:14]1[C:18]([CH3:19])=[C:17]([Cl:21])[C:16]([CH3:20])=[N:15]1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 137982511-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethylpyrazole

Product 1

HCID 137983221-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethyl-4-chloropyrazoleYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a solution of 1-(2-fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethylpyrazole (31.9 g) in chloroform (200 ml) was introduced chlorine gas (7.1 g) for 10 minutes under water-cooling, and then the reaction mixture was stirred for further 30 minutes to effect the chlorination reaction. Removal of the solvent from the reaction solution by distillation in vacuo gave the titled compound (35.2 g) as a pale brown oil. Purification of this oil by silica gel column chromatography yielded a colorless oil. nD23 =1.5431.

Workup

  1. temperaturecooling
  2. customthe chlorination reaction
  3. customRemoval of the solvent from the reaction solution
  4. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-094d6ea7a4884f658cd8493920541ee8
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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