2-Chloro-5-fluoro-1,3-dinitrobenzene → HCID 18444517, compound

HRID 901882Notes

Reaction equation

HRID 901882 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Cu](C#N)[C:16]#[N:17]>CN(C)C=O>[F:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:16]#[N:17])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 123611032-Chloro-5-fluoro-1,3-dinitrobenzeneHCID 178418260HCID 178418260, compound

Product 1

HCID 18444517HCID 18444517, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To 5.39 g (24.44 mmol) of 2-chloro-5-fluoro-1,3-dinitro-benzene dissolved in 20 mL dimethylformamide was added 2.63 g (1.2 eq., 29.27 mmol) copper cyanide. The mixture was stirred at 140° C. for 2 hours, cooled and partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography, eluting with ethyl acetate/hexanes, provided 1.44 g of 4-fluoro-2,6-dinitrobenzonitrile.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washColumn chromatography, eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0965814f88204ae490b9d0cc29d6d152
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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