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

HRID 2182812Notes

Reaction equation

HRID 2182812 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]([O:14][CH:15]([F:17])[F:16])[NH:11][N:10]=1.S(OC)(O[CH3:22])(=O)=O.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[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:15]([F:16])[F:17])[N:11]([CH3:22])[N:10]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 178506403HCID 178506403, compound

Product 1

HCID 156723613-(2,4-Dichlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazoleYield 78.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

457.2 g of 3-(2,4-dichlorophenyl)-5-difluoromethoxy-1H-pyrazole from Example 3.2 were initially charged in 2300 ml of toluene. 227.3 g of dimethyl sulfate were added dropwise, and the mixture was heated at reflux for 3 h. After cooling, 500 ml of saturated aqueous NH4Cl solution were added, the mixture was stirred for 1 h and the organic phase was separated off and washed with water until neutral. Drying over Na2SO4 and concentration gave 377.8 g of 3-(2,4-dichlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole of a purity of 92.9% (GC). Yield: 73.1%. M.p.: 35° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. customthe organic phase was separated off
  5. washwashed with water until neutral
  6. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-57b9525bb8f1406c9480307f6ef4e288
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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