Chlorodifluoromethane → Ethyl 1,1-diethoxyethyl(difluoromethyl)phosphinate

HRID 1463628Notes

Reaction equation

HRID 1463628 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([PH:11](=[O:15])[O:12][CH2:13][CH3:14])([O:8][CH2:9][CH3:10])[CH3:7])[CH3:4].Cl[CH:17]([F:19])[F:18]>O1CCCC1>[CH2:9]([O:8][C:6]([P:11]([CH:17]([F:19])[F:18])(=[O:15])[O:12][CH2:13][CH3:14])([O:5][CH2:3][CH3:4])[CH3:7])[CH3:10]

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 24758Sodium hydrideHCID 178476820HCID 178476820, compound

Product 1

HCID 9992738Ethyl 1,1-diethoxyethyl(difluoromethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 15.8 g of sodium hydride (dispersion in oil) in 500 ml of tetrahydrofuran are added dropwise 67 g (300 mMol) of ethyl 1,1-diethoxyethylphosphinate at such a rate so that the temperature does not exceed 25° C. This mixture is stirred for one hour at room temperature, then cooled to -10° C. and 77.8 g (900 mMol) of chlorodifluoromethane are introduced. Stirring is continued for another 2 hours at room temperature, then 100 ml of ice-cold water are added. The mixture is extracted three times with dichloromethane and the combined extracts dried over magnesium sulphate. Removal of the solvent in vacuo gives ethyl 1,1-diethoxyethyl(difluoromethyl)phosphinate as a viscous oil, Rf=0.44 (CH2Cl2 /CH3COOH, 9+1).

Workup

  1. customdoes not exceed 25° C
  2. temperaturecooled to -10° C.
  3. stirringStirring
  4. waitis continued for another 2 hours at room temperature
  5. extractionThe mixture is extracted three times with dichloromethane
  6. dry with materialthe combined extracts dried over magnesium sulphate
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c0c74fdc3111405993a7c37851007486
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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