1,1-Dichloroethane → 2,4-Dichlorobenzonitrile

HRID 28092

Reaction equation

HRID 28092 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+]([O-])=O)[CH:3]=1.[Cl-].[Li+].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:19]C(Cl)C>CN1CCCC1=O>[Cl:19][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 969244-Chloro-2-nitrobenzonitrileHCID 433294Lithium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 810502,4-DichlorobenzonitrileYield 79.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.55 parts of 4-chloro-2-nitrobenzonitrile, 0.42 parts of lithium chloride, 1.11 parts of anhydrous aluminum chloride and 15 parts of N-methyl-2-pyrrolidone were reacted at 180° C. for 3 hours after the pattern of EXAMPLE B1. The reaction solution was added with 100 parts of dichloroethane, agitated for 30 minutes and filtered. Dichloroethane was distilled off from the filtrate and the residue was added with water to precipitate the crude crystals. The crude crystals were recrystallized by using a water-methanol mixed solvent to obtain 3.4 parts of 2,4-dichlorobenzonitrile with purity of 99%. Yield: 79.2%.

Workup

  1. filtrationfiltered
  2. distillationDichloroethane was distilled off from the filtrate
  3. additionthe residue was added with water
  4. customto precipitate the crude crystals
  5. customThe crude crystals were recrystallized

Sources & evidence

ORD record
ord-402a1150f9fe498699052d6d9e667ac6
Source dataset
uspto-grants-1980_09
Patent number
US04225534

Linked notes

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