Azobisisobutyronitrile → 4-Cyano-3-fluorobenzyl bromide

HRID 2187871Notes

Reaction equation

HRID 2187871 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[F:10])#[N:2].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Br:11])=[CH:5][C:4]=1[F:10])#[N:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 27784664-Cyano-3-fluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-cyano-3-fluorotoluene, as described above in Step C, (5.0 g, 37.0 mmol) in carbon tetrachloride (300 mL) was added N-bromosuccinimide (7.57 g, 42.6 mmol) and 2,2′-azobisisobutyronitrile (610 mg, 3.7 mmol). The reaction mixture was heated to reflux under argon for 24 hrs, then cooled to room temperature, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with a gradient of hexane −4% to 7% EtOAc, to yield the titled product as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under argon for 24 hrs
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of hexane −4% to 7% EtOAc

Sources & evidence

ORD record
ord-97518aec97e84e2b8a624be3e61cd0dc
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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