2-Bromo-5-fluorotoluene → 4-Fluoro-2-methylbenzonitrile
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- temperaturewas refluxed for 24 hours
- extractionextracted with hexane
- dry with materialThe organics were dried over MgSO4
- customthe solvent removed
Sources & evidence
- ORD record
- ord-cf5b6213d93942519cca961bdd767c9f
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093236B2
Reaction notes
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