Chlorobenzene → 4-Chloro-3'-nitrobenzophenone

HRID 1494622Notes

Reaction equation

HRID 1494622 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 8495Benzoyl chloride, 3-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 7673464-Chloro-3'-nitrobenzophenoneYield 76%

Procedure

A mixture of m-nitrobenzoyl chloride 23.25 g (0.12 mol), chlorobenzene 25 ml (0.25 mol) and anhydrous aluminum chloride 17.5 g (0.13 mol) was stirred at 80°-100° C. for 4 hrs. After cooling, the reaction mixture was poured into ice-water with rapid stirring. The white precipitate obtained was collected by filtration and washed with water and then hexane. The white solid was recrystallized from hexane/CH2Cl2 to provide a solid with a melting point of 95°-96° C.; yield 76%.

Workup

  1. temperatureAfter cooling
  2. customThe white precipitate obtained
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customThe white solid was recrystallized from hexane/CH2Cl2
  6. customto provide a solid with a melting point of 95°-96° C.

Sources & evidence

ORD record
ord-5bbb966c955249919fb9001d6a7ea88b
Source dataset
uspto-grants-1991_06
Patent number
US05026872

Reaction notes

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