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

HRID 2255797Notes

Reaction equation

HRID 2255797 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 ) 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-93a5e9c1afee4b0bae4de451404d7402
Source dataset
uspto-grants-1993_08
Patent number
US05241111

Reaction notes

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