Chlorodifluoromethane → HCID 54012352, compound

HRID 1584716Notes

Reaction equation

HRID 1584716 reaction equation
C([O-])(C)(C)C.[K+].[CH3:7][O:8][C:9](=[O:20])[C:10](=[N:18][OH:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].Cl[CH:22]([F:24])[F:23]>COCCOC>[F:23][CH:22]([F:24])[O:19][N:18]=[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]([O:8][CH3:7])=[O:20]

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 23665647Potassium tert-butoxideHCID 73656259HCID 73656259, compound

Product 1

HCID 54012352HCID 54012352, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

At 10-20° C., 28.4 g of potassium tert-butanolate are introduced into a solution of 19.35 g of 2-tolylglyoxylic acid methyl ester oxime in 250 ml of 1,2-dimethoxyethane. As soon as a fine suspension has formed, chlorodifluoromethane is introduced at 25-30° C. After 5 hours, the reaction mixture is concentrated by evaporation in vacuo, water is added to the residue and the product is weakly acidified with 2N hydrochloric acid and extracted several times with ethyl acetate. After washing and concentrating the combined organic phases by evaporation, purification is carried out by flash chromatography (silica gel, ethyl acetate/hexane 1:5), yielding 2-tolylglyoxylic acid methyl ester O-difluoromethyloxime in the form of a yellow oil.

Workup

  1. customAs soon as a fine suspension has formed
  2. concentrationthe reaction mixture is concentrated by evaporation in vacuo, water
  3. additionis added to the residue
  4. extractionextracted several times with ethyl acetate
  5. washAfter washing
  6. concentrationconcentrating the combined organic phases
  7. customby evaporation, purification

Sources & evidence

ORD record
ord-11d4de2f029544648abbb04b3a1344bd
Source dataset
uspto-grants-1999_08
Patent number
US05935908

Reaction notes

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