Water → 4-Chlorophenyl-2,2-difluoroethanoyl chloride

HRID 1080715Notes

Reaction equation

HRID 1080715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:15])([F:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[OH-].[K+].O.C(Cl)(=O)C([Cl:22])=O>C(O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:15])([F:14])[C:9]([Cl:22])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 65578Oxalyl chlorideHCID 21468011Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate

Product 1

HCID 233657314-Chlorophenyl-2,2-difluoroethanoyl chloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-chlorophenyl-2,2-difluoroacetate (250 mg) and potassium hydroxide (300 mg) were mixed in 27 ml of ethanol and 2.4 ml of water and the reaction mixture was refluxed for four hours. The mixture was then acidified and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4 and the solvent was removed in vacuo to give a product which was dissolved in 410 mg of oxalyl chloride with catalytic amount of N,N-dimethylformamide. The mixture was stirred for two hours and excess oxalyl chloride was removed in vacuo to give 4-chlorophenyl-2,2-difluoroethanoyl chloride which was used as is for the subsequent step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. customthe solvent was removed in vacuo
  5. customto give a product which
  6. customexcess oxalyl chloride was removed in vacuo

Sources & evidence

ORD record
ord-9d89a6169e5d4978bb818869452df78f
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

Loading…