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

HRID 1704268Notes

Reaction equation

HRID 1704268 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 twenty-four 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 59°). Mass spectrum (70 ev) mol. ion 186 m/e.

Workup

  1. temperatureis refluxed for twenty-four 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-3d7ff2b6e7634f84afc549af6c8c8548
Source dataset
uspto-grants-1978_11
Patent number
US04126617

Reaction notes

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