Dimethylformamide → HCID 20314466, compound

HRID 2419921Notes

Reaction equation

HRID 2419921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14](O)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O.CN(C)C=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14]([Cl:26])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13384246HCID 13384246, compound

Product 1

HCID 20314466HCID 20314466, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (±)-2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-methylpropionic acid (414 mg.), thionyl chloride (1.0 g.) and dimethylformamide (0.05 g.) in benzene (10 ml.) is heated under reflux for 1 hour. The solvent is evaporated in vacuo, and light petroleum (10 ml., b.p. 60°-80° C.) is added, and the mixture is re-evaporated. A further 10 ml. of light petroleum are added, and the mixture re-evaporated. The residue is dissolved in light petroleum, and the solution is filtered and evaporated to give (±)-2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-methylpropionyl chloride (401 mg.).

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solvent is evaporated in vacuo, and light petroleum (10 ml., b.p. 60°-80° C.)
  3. additionis added
  4. customthe mixture is re-evaporated
  5. additionof light petroleum are added
  6. customthe mixture re-evaporated
  7. dissolutionThe residue is dissolved in light petroleum
  8. filtrationthe solution is filtered
  9. customevaporated

Sources & evidence

ORD record
ord-ebe85dd9b8344f4dbca5c9c9cd3078aa
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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