Dimethylformamide → 2-Fluoro-4-methylbenzonitrile

HRID 1835674Notes

Reaction equation

HRID 1835674 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[CH3:10][N:11](C=O)C>C(OCC)(=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

4

Reactant 2

HCID 6228DimethylformamideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 27784432-Fluoro-4-methylbenzonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-3-fluorotoluene (2 g, 10.6 mmol) and cuprous cyanide (1.4 g, 15.9 mmol) in DMF (15 mL) was heated at reflux for 4 h. The reaction mixture was diluted with ethyl acetate, washed with aqueous ammonia, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:n-hexane, 1:4) to give the title compound (1.0 g, 70%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. washwashed with aqueous ammonia
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (EtOAc:n-hexane, 1:4)

Sources & evidence

ORD record
ord-4bd515afeda9496e8c6b9850fa6fea4e
Source dataset
uspto-grants-2004_08
Patent number
US06774110B2

Reaction notes

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