2-Bromo-5-fluorotoluene → 4-Fluoro-2-methylbenzonitrile

HRID 2193431Notes

Reaction equation

HRID 2193431 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[C:10]([Cu])#[N:11]>CN(C=O)C.O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]#[N:11])=[C:3]([CH3:9])[CH:4]=1

Participants

5

Reactant 2

HCID 967432-Bromo-5-fluorotolueneHCID 178418546HCID 178418546, compound

Product 1

HCID 38260554-Fluoro-2-methylbenzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-5fluorotoluene (3.5 g, 18.5 mmol) and CuCN (2 g, 22 mmol) in DMF (100 mL) was refluxed for 24 hours. The reaction was diluted with water and extracted with hexane. The organics were dried over MgSO4 and the solvent removed to give product 31 (yield 60%). 1H-NMR (400 MHz, CDCl3): δ 7.60 (dd, J=5.6, 8.8 Hz, 1H), 6.93-7.06 (m, 2H), 2.55 (s, 3H).

Workup

  1. temperaturewas refluxed for 24 hours
  2. extractionextracted with hexane
  3. dry with materialThe organics were dried over MgSO4
  4. customthe solvent removed

Sources & evidence

ORD record
ord-3729138152b441f9be84b0b7f14dc785
Source dataset
uspto-grants-2012_12
Patent number
US08329900B2

Reaction notes

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