Dimethylformamide → 2-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride

HRID 2419902Notes

Reaction equation

HRID 2419902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14]([C:22]([F:25])([F:24])[F:23])([C:18]([F:21])([F:20])[F:19])[C:15](O)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:30])=O.CN(C)C=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]([C:18]([F:19])([F:20])[F:21])([C:22]([F:24])([F:25])[F:23])[C:15]([Cl:30])=[O:16])=[CH:26][CH:27]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 133842612-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid

Product 1

HCID 203144652-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid (3.0 g.), thionyl chloride (3.0 ml.), dimethylformamide (0.16 g.) and benzene (10 ml.) is heated under reflux until the solution becomes turbid (ca. 10 minutes). The mixture is evaporated in vacuo, benzene (10 ml.) is added and the evaporation is repeated. Light petroleum (10 ml., b.p. 40°-60° C.) is added to the residue, and the solution is separated from insoluble oils and evaporated to give 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride (3.07 g.), m.p. 30°-35° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux until the solution
  3. customturbid (ca. 10 minutes)
  4. customThe mixture is evaporated in vacuo, benzene (10 ml.)
  5. additionis added
  6. customthe evaporation
  7. additionLight petroleum (10 ml., b.p. 40°-60° C.) is added to the residue
  8. customthe solution is separated from insoluble oils
  9. customevaporated

Sources & evidence

ORD record
ord-a554bfd4ee514b218fdbcaa7ac387c16
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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