Potassium Fluoride → 2-Chloro-4,5-difluorobenzonitrile

HRID 1729485

Reaction equation

HRID 1729485 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](Cl)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[F-:12].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([F:12])[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 27827532,4-Dichloro-5-fluorobenzonitrile

Product 1

HCID 40858492-Chloro-4,5-difluorobenzonitrileYield 68.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture comprising 5.70 g (0.03 mol) of 2,4-dichloro-5-fluorobenzonitrile, 3.48 g (0.06 mol) of spray dried KF and 30 ml of dimethylsulfoxide, was reacted at a temperature of from 140° to 150° C. for 3.5 hours in a glass reactor. After completion of the reaction, the mixture was poured into ice water (50 ml) and extracted with chloroform. The chloroform extract was washed five times with water and then dried. Then chloroform was distilled off. The residue was distilled under reduced pressure to obtain 3.57 g (yield: 68.6%) of 2-chloro-4,5-difluorobenzonitrile. Boiling point: 105°-107° C./37 mmHg; melting point: 35°-37° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. washwas washed five times with water
  5. customdried
  6. distillationThen chloroform was distilled off
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-6bc9dc00baca4272a4c1fb4f5e1ef79e
Source dataset
uspto-grants-1994_07
Patent number
US05332851

Linked notes

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