Chlorodifluoromethane → HCID 11357876, compound

HRID 2182809Notes

Reaction equation

HRID 2182809 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([CH3:14])[N:9]=2)=[C:4]([F:15])[CH:3]=1.[OH-].[Na+].Cl[CH:19]([F:21])[F:20]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH:19]([F:21])[F:20])[N:10]([CH3:14])[N:9]=2)=[C:4]([F:15])[CH:3]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 178481736HCID 178481736, compound

Product 1

HCID 11357876HCID 11357876, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

57.1 g of 3-(4-chloro-2-fluorophenyl)-5-hydroxy-1-methyl-1H-pyrazole from Example 2.1 were initially charged in 500 ml of dioxane. A solution of 18.8 g of NaOH in 50 ml of H2O was added, the mixture was heated at reflux and 85 g (0.98 mol=3.9 eq.) of gaseous chlorodifluoromethane were introduced. The mixture was poured into 1.5 l of water and extracted twice with 500 ml of MTBE, and the combined organic phases were extracted once with 500 ml of water and once with 500 ml of saturated sodium chloride solution. Drying and concentration of the organic phase gave 57.6 g of 53% pure 3-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole as an oil which was purified further by vacuum distillation. This gave the title compound in a purity of 94% in a yield of 43.8%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. extractionextracted twice with 500 ml of MTBE
  4. extractionthe combined organic phases were extracted once with 500 ml of water and once with 500 ml of saturated sodium chloride solution
  5. customDrying

Sources & evidence

ORD record
ord-fa01c0f2003140dd8048afef86c570cf
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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