Water → Benzene, 2-fluoro-1,3-dinitro-

HRID 1076988Notes

Reaction equation

HRID 1076988 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[F-:14].[K+].CN(C)C=O.O>C(Cl)Cl>[F:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 118141-Chloro-2,6-dinitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 11171409Benzene, 2-fluoro-1,3-dinitro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-chloro-2,6-dinitrobenzene (30 grams), anhydrous potassium fluoride (35 grams), and dimethylformamide (50 ml.) is refluxed for 24 hours. The reaction mixture is poured into water (250 ml.) and extracted with ether (3 × 100 ml.). The combined ether extracts are dried with anhydrous sodium sulfate. Removal of the solvent leaves brown solid. Chromatography of the solid on silica gel with methylene chloride as the elutant gives a light yellow solid after recrystallization from pentane-methylene chloride. (20.30 grams, melting point 50°).

Workup

  1. temperatureis refluxed for 24 hours
  2. extractionextracted with ether (3 × 100 ml.)
  3. dry with materialThe combined ether extracts are dried with anhydrous sodium sulfate
  4. customRemoval of the solvent
  5. customleaves brown solid
  6. customafter recrystallization from pentane-methylene chloride

Sources & evidence

ORD record
ord-258cd5e4c3204e33a7f08e182879e935
Source dataset
uspto-grants-1976_05
Patent number
US03959289

Reaction notes

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