Azobisisobutyronitrile → 3'-Bromo-4'-(bromomethyl)biphenyl-2-carbonitrile

HRID 1379871Notes

Reaction equation

HRID 1379871 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][Br:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 218403383'-Bromo-4'-methyl-1,1'-biphenyl-2-carbonitrile

Product 1

HCID 218403713'-Bromo-4'-(bromomethyl)biphenyl-2-carbonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1.0 g (3.7 mmol) of 3'-bromo-4'methyl-1,1'-biphenyl-2-nitrile (Step C) in 15 mL of carbon tetrachloride under a nitrogen atmosphere was treated with 0.720 g (4.04 mmol) of N-bromosuccinimide followed by 60 mg (0.37 mmol) of azobisisobutyronitrile (AIBN). The reaction mixture was heated at reflux for four hours, cooled to room temperature and filtered through Celite. The solvent was removed under vacuum and the residue was dissolved in methylene chloride and treated with decolorizing carbon. The solids were filtered through Celite and the solvent removed under vacuum. The resulting solid was triturated with cold ether, filtered and air dried to afford 920 mg (71%) of the product as an off-white solid. 1H NMR (200 MHz, CDCl3): δ 4.64 (s, 2H), 7.4-7.8 (m, 7H). EI-MS: calculated for C14H9Br2N 351; found 351 (M+, 20%); 271 (M-Br, 100%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for four hours
  3. filtrationfiltered through Celite
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue was dissolved in methylene chloride
  6. additiontreated with decolorizing carbon
  7. filtrationThe solids were filtered through Celite
  8. customthe solvent removed under vacuum
  9. customThe resulting solid was triturated with cold ether
  10. filtrationfiltered
  11. customair dried

Sources & evidence

ORD record
ord-14e5028674c548dba6f108ebfc7e99ed
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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