3-Fluoro-5-bromobenzaldehyde oxime → 3-Bromo-5-fluorobenzonitrile

HRID 496668Notes

Reaction equation

HRID 496668 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

HCID 738580123-Fluoro-5-bromobenzaldehyde oxime

Product 1

HCID 27833303-Bromo-5-fluorobenzonitrileYield 89.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolvent

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

  1. temperatureheated
  2. temperatureunder reflux
  3. customthe mixture was evaporated
  4. washwashed with sulfuric acid (1N), water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-97cbebec96c34173bbc7a0eaa2535c6c
Source dataset
uspto-grants-2005_09
Patent number
US06946454B2

Reaction notes

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