Azobisisobutyronitrile → 4-Bromomethyl-2-trifluoromethylbenzonitrile

HRID 1441685Notes

Reaction equation

HRID 1441685 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27755974-Methyl-2-(trifluoromethyl)benzonitrile

Product 1

HCID 591645854-Bromomethyl-2-trifluoromethylbenzonitrileYield 157.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing mixture of 5.0 g 4-Methyl-2-(trifluoromethyl)benzonitrile in 50 ml tetrachloromethane were added a mixture of 5.77 g N-bromosuccinimide and 1.77 g 2,2′-azobis(2-methylpropionitrile). The reaction mixture was heated under reflux for three hours. The reaction mixture was filtered through a pad of celite and the solvent was removed in vacuo to obtain 11.2 g crude 4-Bromomethyl-2-trifluoromethyl-benzonitrile (impurified with the dibromo product) as a white solid. This material was used without further purification.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for three hours
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f1dbe9fd966e46c483507ca4ba370b6e
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

Loading…