Chlorodifluoromethane → HCID 14796596, compound

HRID 973688Notes

Reaction equation

HRID 973688 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11](=[O:13])[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH:17]([F:19])[F:18]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH:17]([F:19])[F:18])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 6068793-(4-Chlorophenyl)-1,2-oxazol-5(4H)-one

Product 1

HCID 14796596HCID 14796596, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 100 ml autoclave, 5.87 g (0.03 mol) 3-(4-chlorophenyl)-5-(4H)-isoxazolone was dissolved 30 ml dioxane and treated with 10 ml of 30% aqueous potassium hydroxide. The autoclave was pressurised to 10 bar with chlorodifluoromethane and the reaction mixture was heated at 50°-60° C. for 15 hours. After cooling and reducing the pressure the solution was poured into 300 ml ice/water and extracted three times with 70 ml ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by column chromatography.

Workup

  1. temperaturethe reaction mixture was heated at 50°-60° C. for 15 hours
  2. temperatureAfter cooling
  3. extractionextracted three times with 70 ml ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-47f31dbd9435406b9cfc398dfe522e15
Source dataset
uspto-grants-1991_11
Patent number
US05064847

Reaction notes

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