Nitric Acid → 4-chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 277407Notes

Reaction equation

HRID 277407 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([Cl:20])=[CH:14][C:13]=2[F:21])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].S(=O)(=O)(O)O.[N+:27]([O-])([OH:29])=[O:28]>>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:21])=[CH:14][C:15]([Cl:20])=[C:16]([O:18][CH3:19])[C:17]=2[N+:27]([O-:29])=[O:28])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 186156481-Methyl-3-(2-fluoro-4-chloro-5-methoxyphenyl)-4-chloro-5-trifluoromethyl-1H-pyrazole

Product 1

HCID 186156314-chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

Procedure

4-Chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole (1.2 g, 3.5 mmol) was slurried with 4 ml of con. sulfuric acid and was slowly added to a stirred 4 ml mixture of con. sulfuric acid-con. nitric acid (9:1) at −15° C. Solution was allowed to stir at ambient temperature for 2 hr and then added to ice water. Extraction with ethyl acetate and removal of the solvent afforded a crude product which was chromatographed on silica gel. Elution of the column with hexane-methylene chloride (4:6) furnished the title compound (0.72 g).

Workup

  1. customat −15° C
  2. extractionExtraction
  3. customwith ethyl acetate and removal of the solvent
  4. customafforded a crude product which
  5. customwas chromatographed on silica gel
  6. washElution of the column with hexane-methylene chloride (4:6)

Sources & evidence

ORD record
ord-647a9001a7234a14b16b98830c35d64f
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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