Sulfuryl chloride → 4-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

HRID 2395635Notes

Reaction equation

HRID 2395635 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[C:12]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:14]([CH3:21])[N:13]=1.S(Cl)([Cl:25])(=O)=O>C(O)(=O)C.O>[Cl:25][C:16]1[C:12]([C:3]2[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[F:1])=[N:13][N:14]([CH3:21])[C:15]=1[C:17]([F:18])([F:19])[F:20]

Participants

5

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 152785683-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 152785694-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 5.00 g of 3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole dissolved in 50 ml of acetic acid was added 15 ml of sulfuryl chloride. The mixture was mildly refluxed with 2 ml portions of sulfuryl chloride added every 15 minutes. After 6 hours, the mixture was cooled, then diluted with water and extracted with ether. The ether was washed 3 times with water, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was chromatographed to give a quantitative yield of 4-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole.

Workup

  1. additionadded every 15 minutes
  2. temperaturethe mixture was cooled
  3. extractionextracted with ether
  4. washThe ether was washed 3 times with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed

Sources & evidence

ORD record
ord-55895fc91ed54b7aaa118dca09c24769
Source dataset
uspto-grants-1996_02
Patent number
US05489571

Reaction notes

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