1,4-Dichlorobenzene → 2,5-Dichlorobenzophenone
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:20]Participants
4
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 5.4 g of 1,4-dichlorobenzene, 4.2 g of aluminum chloride and 0.5 ml of benzoyl chloride was stirred at 170° C. Additional benzoyl chloride, up to a total of 4 g, was slowly added to the mixture over 2.5 hours, and the resulting mixture was stirred for another hour at 170° C. The molar ratio of reactants was 1.1/1.3/ (AClCl3 :Dichlorobenzene:Benzoyl Chloride). After work-up of the crude mixture as in Examples 7 through 10, 2,5-dichlorobenzophenone was obtained in 64% yield, as determined by gas chromatography using 3-chlorobenzophenone as the internal standard.
Workup
- stirringthe resulting mixture was stirred for another hour at 170° C
Sources & evidence
- ORD record
- ord-dbe583c0689442d1be02a717f513dd98
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210313
Reaction notes
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