Ammonia → 3,4,5-Trifluorobenzonitrile

HRID 1675574Notes

Reaction equation

HRID 1675574 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 resulting mixture was stirred at 150° C. for 4 hours. Thereafter, aqueous ammonia was added to the reaction mixture which had been allowed to cool to near room temperature, followed by extraction 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, and 5.0 g of 3,4,5-trifluorobenzonitrile was obtained.

Workup

  1. temperatureto cool to near room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac3874f398304c0cbf7d61a32ffb7f45
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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