Thionyl Chloride → 1,1'-(Chloromethylene)bis(4-fluorobenzene)

HRID 414485

Reaction equation

HRID 414485 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([Cl:19])[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1230494,4'-Difluorobenzhydryl alcohol

Product 1

HCID 27237731,1'-(Chloromethylene)bis(4-fluorobenzene)Yield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15.0 g (68.1 mmol) of 4,4'-difluorobenzhydrol was added 14.9 ml (204 mmol) of thionyl chloride in the atmosphere of argon, and the mixture was stirred at room temperature for 30 minutes. To the resulting mixture was added water followed by extraction with benzene. The organic layer was successively washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to column chromatography on silica gel. There was yielded 14.32 g (60 mmol) of 4,4'-difluorobenzhydryl chloride from the fraction eluted with benzene.

Workup

  1. extractionfollowed by extraction with benzene
  2. washThe organic layer was successively washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-f399839528ef486585527d95483c9819
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Linked notes

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