Thionyl Chloride → HCID 20314483, compound

HRID 973316Notes

Reaction equation

HRID 973316 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]([C:15]([F:18])([F:17])[F:16])([C:11]([F:14])([F:13])[F:12])[C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]([C:15]([F:18])([F:17])[F:16])([C:11]([F:14])([F:13])[F:12])[C:8]([Cl:23])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 133842322-(4-Chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid

Product 1

HCID 20314483HCID 20314483, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionic acid (161 mg.), thionyl chloride (200 mg.), dimethylformamide (20 mg.) and light petroleum (2 ml. b.p. 40°-60° C.) is heated under reflux for 15 minutes and the solvent evaporated. Light petroleum (5 ml. is added, and the evaporation repeated. The residue is dissolved in light petroleum, the solution filtered and evaporated to give 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride (151 mg.) as an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 minutes
  3. customthe solvent evaporated
  4. additionis added
  5. customthe evaporation
  6. dissolutionThe residue is dissolved in light petroleum
  7. filtrationthe solution filtered
  8. customevaporated

Sources & evidence

ORD record
ord-0e25f6e2992f4a6f807bbc50db084436
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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