Thionyl Chloride → 1-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzene

HRID 2082674Notes

Reaction equation

HRID 2082674 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClC(Cl)Cl>[Cl:3][CH:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27774043-(Trifluoromethyl)benzhydrol

Product 1

HCID 5968291-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 40 parts of sulfinyl chloride in 150 parts of trichloromethane is added dropwise a solution of 64 parts of α-phenyl-3-(trifluoromethyl)benzenemethanol in 375 parts of trichloromethane. Upon completion, stirring is continued for 1 hour at room temperature. The whole is heated to reflux and stirring is continued for 3 hours at reflux temperature. After stirring overnight at room temperature, the solvent is evaporated. The residue is taken up in methylbenzene and the latter is evaporated again, yielding 70 parts (100%) of 1-(chlorophenylmethyl)-3-(trifluoromethyl)benzene as an oily residue.

Workup

  1. temperatureThe whole is heated
  2. temperatureto reflux
  3. stirringstirring
  4. waitis continued for 3 hours
  5. temperatureat reflux temperature
  6. stirringAfter stirring overnight at room temperature
  7. customthe solvent is evaporated
  8. customthe latter is evaporated again

Sources & evidence

ORD record
ord-83a79e8b53454c84ae64437917732ccd
Source dataset
uspto-grants-1978_04
Patent number
US04082755

Reaction notes

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