Pyrazole → methyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoate

HRID 1086747Notes

Reaction equation

HRID 1086747 reaction equation
[OH-].[K+].CI.[Cl:5][C:6]1[CH:14]=[C:13]([F:15])[C:12]([C:16]2[C:20]([Cl:21])=[C:19]([O:22][CH:23]([F:25])[F:24])[N:18]([CH3:26])[N:17]=2)=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].N1C=C[CH:29]=N1>CC(C)=O>[Cl:5][C:6]1[CH:14]=[C:13]([F:15])[C:12]([C:16]2[C:20]([Cl:21])=[C:19]([O:22][CH:23]([F:24])[F:25])[N:18]([CH3:26])[N:17]=2)=[CH:11][C:7]=1[C:8]([O:10][CH3:29])=[O:9]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 156719592-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoic acid

Product 1

HCID 15671960methyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoateYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A KOH powder (0.1 g, 1.8 mmoles) and methyl iodide (0.26 g, 1.8 mmols) were added to a solution of 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoic acid (0.30 g, 0.8 moles) in 20 ml acetone and reacted with this pyrazole derivative under reflux 3 hours. Then the extraction with ethylacetate, washing with water, dehydration, and concentration of the extract solution, and purification of the residue by column chromatography gave the title compound (0.15 g), yield 48%.

Workup

  1. temperatureunder reflux 3 hours
  2. extractionThen the extraction with ethylacetate
  3. washwashing with water, dehydration, and concentration of the extract solution, and purification of the residue by column chromatography

Sources & evidence

ORD record
ord-b96d1263fd3f420ab8aa073eec8e0ecb
Source dataset
uspto-grants-1991_07
Patent number
US05032165

Reaction notes

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