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

HRID 417797

Reaction equation

HRID 417797 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-5-fluorotoluene (2) (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 3 (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-cf5b6213d93942519cca961bdd767c9f
Source dataset
uspto-grants-2012_01
Patent number
US08093236B2

Linked notes

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