Ammonia → 2-Fluoro-4-methylbenzonitrile

HRID 1668926Notes

Reaction equation

HRID 1668926 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[C:10]([Cu])#[N:11].N.C(OCC)C>CN(C=O)C>[F:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:10]#[N:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 5732804-Bromo-3-fluorotolueneHCID 178418546HCID 178418546, compound

Product 1

HCID 27784432-Fluoro-4-methylbenzonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-bromo-2-fluoro-4-methylbenzene (70 g, 370 mmol) and CuCN (50 g, 555 mmol) in DMF (300 mL) was heated at reflux for 24 h. After cooling to RT, concentrated aqueous ammonia (300 mL) and diethyl ether (200 mL) were added and the mixture stirred for 1 h. The mixture was extracted with diethyl ether (3×200 mL). The combined organic layers were washed with brine (3×200 mL) and dried over sodium sulfate. Solvent was removed in vacuo to give the product (44 g, 88%) as pale yellow solid. MS (M+H)+ 136.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. extractionThe mixture was extracted with diethyl ether (3×200 mL)
  4. washThe combined organic layers were washed with brine (3×200 mL)
  5. dry with materialdried over sodium sulfate
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-0eb3e230c6a34df3b34d7bfd4d606c43
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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