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

HRID 973301Notes

Reaction equation

HRID 973301 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-06d23d95d060492fb7ff67b56559362d
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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