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

HRID 990658Notes

Reaction equation

HRID 990658 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-364c7f6322e542ddb53d2c3a313dce7e
Source dataset
uspto-grants-2002_10
Patent number
US06462032B1

Reaction notes

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