Tetracyanoethylene → HCID 66839327, compound

HRID 546766Notes

Reaction equation

HRID 546766 reaction equation
ClCCO[CH:5]([O:13][CH2:14][CH2:15][Cl:16])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.C[Si]([C:21]#[N:22])(C)C.C(C(C#N)=C(C#N)C#N)#N>C(#N)C>[Cl:16][CH2:15][CH2:14][O:13][CH:5]([C:6]1[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=1)[C:21]#[N:22]

Participants

5

Reactant 3

HCID 12635TetracyanoethyleneHCID 82115Trimethylsilyl cyanideHCID 66839257HCID 66839257, compound

Product 1

HCID 66839327HCID 66839327, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution containing 1-[bis-(2-chloroethoxy)methyl]-4-fluorobenzene (5.43 g), trimethylsilyl cyanide (4.06 mL) and tetracyanoethylene (520 mg) in acetonitrile (100 mL) was heated under reflux for four hours. The reaction solution was returned to room temperature and the solvent was evaporated under reduced pressure. Ethyl acetate and brine were added to the residue, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane/ethyl acetate) to obtain the title compound (4.3 g). The property values of the compound are as follows.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for four hours
  3. customwas returned to room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate and brine were added to the residue
  6. customthe organic layer was separated
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-c06382617f5b4bae89642252df053480
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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