Azobisisobutyronitrile → 2-(4-Bromomethylphenyl)4-chlorobenzonitrile

HRID 487996Notes

Reaction equation

HRID 487996 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:3]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=2[C:6]#[N:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 224179974-Chloro-2-(4-methylphenyl)benzonitrile

Product 1

HCID 224180002-(4-Bromomethylphenyl)4-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6.83 g of 4-chloro-2-(4-methylphenyl)benzonitrile, 5.34 g of N-bromosuccinimide and 0.1 g of α,α'-azobis(isobutyronitrile) were heated in 220 ml of carbon tetrachloride under reflux for 2 hr. The succinimide was removed by filtration, and the filtrate was concentrated. The residue was crystallized from a mixed solvent of tetrahydrofuran-isopropyl ether. The yield was 5.6 g.

Workup

  1. temperatureunder reflux for 2 hr
  2. customThe succinimide was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was crystallized from a mixed solvent of tetrahydrofuran-isopropyl ether

Sources & evidence

ORD record
ord-69f01f20e248435cbe1493319125a183
Source dataset
uspto-grants-1994_03
Patent number
US05298518

Reaction notes

Loading…