Ammonia → 3,4,5-Trifluorobenzonitrile

HRID 2236370Notes

Reaction equation

HRID 2236370 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[Cu](C#N)[C:12]#[N:13].N>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:9])[C:7]=1[F:8])[C:12]#[N:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 178418260HCID 178418260, compound

Product 1

HCID 5938143,4,5-TrifluorobenzonitrileYield 67.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To 50 ml of N-methylpyrrolidone were added 10 g of 3,4,5-trifluorobromobenzene and 8.5 g of copper cyanide and the mixture obtained was stirred at 150° C. for 4 hours. Then, aqueous ammonia was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.0 g of 3,4,5-trifluorobenzonitrile.

Workup

  1. customthe mixture obtained
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af8a074d36d04fca83136d188fce5e8b
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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