1,3-Dichlorobenzene → (2-Chloro-5-nitrophenyl)(2,4-dichlorophenyl)methanone

HRID 1111347Notes

Reaction equation

HRID 1111347 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8](Cl)=[O:9].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][C:21]=1[Cl:25])=[O:9]

Participants

5

Reactant 3

HCID 109431,3-DichlorobenzeneHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 15072475(2-Chloro-5-nitrophenyl)(2,4-dichlorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

6 g of aluminium chloride are added to 5 g of 2-chloro-5-nitrobenzoyl chloride in 60 ml of dichloromethane, and 30 ml of 1,3-dichlorobenzene are then added dropwise. The reaction medium is heated for 2 hours at 80° C. and then cooled, and poured onto crushed ice. After extracting with dichloromethane, washing with water and drying over sodium sulphate, the organic phase is evaporated to dryness under vacuum and the crystalline residue is recrystallized in cyclohexane (3.6 g).

Workup

  1. additionare then added dropwise
  2. temperaturecooled
  3. additionpoured
  4. customonto crushed ice
  5. extractionAfter extracting with dichloromethane
  6. washwashing with water
  7. dry with materialdrying over sodium sulphate
  8. customthe organic phase is evaporated to dryness under vacuum
  9. customthe crystalline residue is recrystallized in cyclohexane (3.6 g)

Sources & evidence

ORD record
ord-0d56004845d840a3ab249254ecea94eb
Source dataset
uspto-grants-1990_12
Patent number
US04980349

Reaction notes

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