Pentafluorobenzonitrile → 2,3,5,6-Tetrafluoro-4-methoxybenzonitrile

HRID 358872Notes

Reaction equation

HRID 358872 reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]1[C:10]([C:11]#[N:12])=[C:9]([F:13])[C:8]([F:14])=[C:7](F)[C:6]=1[F:16]>CO>[CH3:1][O:2][C:7]1[C:6]([F:16])=[C:5]([F:4])[C:10]([C:11]#[N:12])=[C:9]([F:13])[C:8]=1[F:14]

Participants

4

Reactant 2

HCID 69882PentafluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 144572672,3,5,6-Tetrafluoro-4-methoxybenzonitrileYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 44.8 g (0.83 mole) of sodium methoxide in 1.6 liters of methanol was added dropwise at room temperature to a solution of 160.0 g (0.83 mole) of pentafluorobenzonitrile (XVIII) in 2.5 liters of methanol, whilst stirring. When the addition was complete, the mixture was allowed to stand at room temperature overnight. At the end of this time, the solvent was removed by evaporation under reduced pressure, and the residue was shaken with a mixture of water and toluene. The toluene layer was separated, washed with water and dried over anhydrous sodium sulfate; the solvent was then removed by evaporation under reduced pressure. The residual solid was washed with hexane to afford 160.7 g of 4-methoxy-2,3,5,6-tetrafluorobenzonitrile (XIX) as colorless needles.

Workup

  1. additionWhen the addition
  2. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  3. stirringthe residue was shaken with a mixture of water and toluene
  4. customThe toluene layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was then removed by evaporation under reduced pressure
  8. washThe residual solid was washed with hexane

Sources & evidence

ORD record
ord-6e74522ab1fb41a68dab732449db36b8
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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