6-Chloro-2-nitrobenzonitrile → 2-Chloro-6-fluorobenzonitrile

HRID 1448012Notes

Reaction equation

HRID 1448012 reaction equation
[F-:1].[K+].[Cl-].C(CCCCCCCCCCCC[NH3+])C1C=CC=CC=1.[N+]([C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:28]=1[C:29]#[N:30])([O-])=O>O.C1(C)C=CC=CC=1>[Cl:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:27]([F:1])[C:28]=1[C:29]#[N:30]

Participants

6

Reactant 3

HCID 810536-Chloro-2-nitrobenzonitrileHCID 522689Potassium FluorideHCID 70600921HCID 70600921, compound

Product 1

HCID 695872-Chloro-6-fluorobenzonitrileYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 120 g (2 mols) of potassium fluoride in 100 ml of water was treated first with 30 ml of a 50% strength aqueous solution of benzyldodecyl-ammonium chloride and then with a solution of 186 g (1 mol) of 2-nitro-6-chloro-benzonitrile in 250 ml of toluene. The reaction mixture was heated to 105° C. for 8 hours. After cooling, the organic phase was separated off and the aqueous phase was extracted with chloroform. The organic phase and the chloroform extracts were combined and washed and then freed from the organic solvent by distillation. On distillation of the residue, 35 g of 2-chloro-6-fluoro-benzonitrile (boiling point: 105°-108° C./15 mm Hg) were obtained.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with chloroform
  4. washwashed
  5. distillationfreed from the organic solvent by distillation
  6. distillationOn distillation of the residue

Sources & evidence

ORD record
ord-7c8797a54d444843a96a621ed00597cc
Source dataset
uspto-grants-1979_12
Patent number
US04179461

Reaction notes

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