Fluorobenzene → 2,4-Dichloro-4'-fluorobenzophenone

HRID 354969Notes

Reaction equation

HRID 354969 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>>[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)=[O:16]

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2847592,4-Dichloro-4'-fluorobenzophenone

Procedure

To a stirred mixture of 20 parts of aluminium chloride and 100 parts of fluorobenzene are added dropwise 20.5 parts of 2,4-dichlorobenzoyl chloride. Upon completion, the mixture is heated to reflux and stirred at reflux temperature for 5 minutes. The reaction mixture is poured onto crushed ice and the product is extracted with 1,1'-oxybisethane. The extract is dried and evaporated, yielding 30 parts of (2,4-dichlorophenyl)(4-fluorophenyl) methanone as an oily residue.

Workup

  1. temperatureUpon completion, the mixture is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature for 5 minutes
  4. additionThe reaction mixture is poured
  5. customonto crushed ice
  6. extractionthe product is extracted with 1,1'-oxybisethane
  7. customThe extract is dried
  8. customevaporated

Sources & evidence

ORD record
ord-b052205fc45f4c8c8361c7c74f1c80e3
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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