Water → 3-(2,4-Dichlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

HRID 2182814Notes

Reaction equation

HRID 2182814 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([OH:14])[N:11]([CH3:15])[N:10]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:23]([F:25])[F:24].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([O:14][CH:23]([F:25])[F:24])[N:11]([CH3:15])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 178481735HCID 178481735, compound

Product 1

HCID 156723613-(2,4-Dichlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazoleYield 94%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

9 g of 3-(2,4-dichlorophenyl)-5-hydroxy-1-methyl-1H-pyrazole from Example 4.1 were initially charged in 50 ml of dimethylacetamide, and 5.4 g of potassium carbonate were added. The mixture was heated at 90° C., and 48 g of gaseous chlorodifluoromethane were introduced over a period of 1 h. The mixture was poured into 800 ml of water and extracted twice with 300 ml of MTBE, and the combined organic phases were extracted once with 100 ml of water and once with 100 ml of saturated sodium chloride solution. Drying and concentration of the organic phase gave 10.2 g of 3-(2,4-dichlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole of a purity of 56% (yield 50.2%, based on the title compound), which was purified further by vacuum distillation.

Workup

  1. extractionextracted twice with 300 ml of MTBE
  2. extractionthe combined organic phases were extracted once with 100 ml of water and once with 100 ml of saturated sodium chloride solution
  3. customDrying

Sources & evidence

ORD record
ord-c8355fcfd6ab4689a919a179a6e43e1a
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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