Azobisisobutyronitrile → 6-Bromo-2-(bromomethyl)quinoline

HRID 271681Notes

Reaction equation

HRID 271681 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[Br:13]N1C(=O)CCC1=O.[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[C:27]([CH3:32])[CH:26]=[CH:25]2>C(Cl)(Cl)(Cl)Cl>[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[C:27]([CH2:32][Br:13])[CH:26]=[CH:25]2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5228856-Bromo-2-methylquinoline

Product 1

HCID 589705326-Bromo-2-(bromomethyl)quinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

148 mg (1.00 mmol) α,α-azoisobutyronitrile and 8.01 g (45.0 mmol) N-bromosuccinimide are added successively to a solution of 10.0 g (45.0 mmol) 6-bromo-2-methyl-quinoline in 60 mL carbon tetrachloride. The reaction mixture is refluxed for 8 h. It is filtered and the filtrate is washed twice with water. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (PE/EtOAc 4:1).

Workup

  1. temperatureThe reaction mixture is refluxed for 8 h
  2. filtrationIt is filtered
  3. washthe filtrate is washed twice with water
  4. dry with materialThe organic phase is dried over MgSO4
  5. customThe purification

Sources & evidence

ORD record
ord-db2786f5491b42db8a1a82a6a28f7cd1
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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