4-Chloro-3,5-dinitrobenzonitrile → 4-Fluoro-3,5-dinitrobenzonitrile

HRID 1710212Notes

Reaction equation

HRID 1710212 reaction equation
[F-:1].[K+].Cl[C:4]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]>>[F:1][C:4]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 160084-Chloro-3,5-dinitrobenzonitrileHCID 522689Potassium Fluoride

Product 1

HCID 136434684-Fluoro-3,5-dinitrobenzonitrileYield 5%

Conditions

Temperature
150 °C

Procedure

A mixture of 7.0 parts of anhydrous potassium fluoride and 5.0 parts of 4-chloro-3,5-dinitrobenzonitrile was heated and maintained at about 150° C., with stirring, for a period of about 6 hours, under a positive pressure of nitrogen. The reaction mixture, a viscous, dark brown liquid was filtered and washed with methylene chloride. Analysis of the filtrate by gas chromatographic techniques indicated a 69% conversion and a 5% yield of 4-fluoro-3,5-dinitrobenzonitrile.

Workup

  1. temperaturewas heated
  2. filtrationThe reaction mixture, a viscous, dark brown liquid was filtered
  3. washwashed with methylene chloride

Sources & evidence

ORD record
ord-3a407875ffa94f56a52a4091a8e7050a
Source dataset
uspto-grants-1990_08
Patent number
US04952719

Reaction notes

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