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

HRID 661321Notes

Reaction equation

HRID 661321 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-fluorotoluene2×HCID 178418546HCID 178418546, compound

Product 1

HCID 38260554-Fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound B was prepared by refluxing a mixture of 2-bromo-5-fluoro-toluene (Compound A) (3.5 g, 18.5 mmol) and CuCN (2 g, 22 mmol) in DMF (100 mL) 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 B (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. temperatureby refluxing
  2. extractionextracted with hexane
  3. dry with materialThe organics were dried over MgSO4
  4. customthe solvent removed

Sources & evidence

ORD record
ord-c77ad11c415549338dac255014dc72ac
Source dataset
uspto-grants-2011_12
Patent number
US08084605B2

Reaction notes

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