3-Fluoro-5-bromobenzaldehyde oxime → 3-Bromo-5-fluorobenzonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[CH:5]=[N:6]O>C(#N)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]#[N:6]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The above oxime (3.76 g, 17.24 mmol) and copper (II) acetate (370 mg) were dissolved in acetonitrile (100 cm3) under nitrogen and heated under reflux. After 5 h, the mixture was evaporated, the residue taken into EtOAc, washed with sulfuric acid (1N), water, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromobenzonitrile (3.08 g, 15.39 mmol, 89%) which was used without further purification.
Workup
- temperatureheated
- temperatureunder reflux
- customthe mixture was evaporated
- washwashed with sulfuric acid (1N), water, brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-09c0fd12d8af423d9f04780d9705f1c8
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091234B2
Reaction notes
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