Azobisisobutyronitrile → 2-[2-(Bromomethyl)phenyl]naphthalene

HRID 1006081Notes

Reaction equation

HRID 1006081 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][Br:18]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 210519422-(2-Naphthyl)toluene

Product 1

HCID 226765282-[2-(Bromomethyl)phenyl]naphthalene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

105 g (0.48 mol) of 13 and 90 g (0.5 mol) of N-bromosuccinimide were dissolved at room temperature in 2000 cm3 of carbon tetrachloride, admixed with 3 g of azobisisobutyronitrile and heated under reflux for 4 hours. The precipitated succinimide was filtered off, the solvent was removed under reduced pressure and the residue was purified by filtration through 1000 g of silica gel (hexane/methylene chloride 9:1). This gave 112 g (79%) of 14 as a colorless, lacrymatory oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe precipitated succinimide was filtered off
  4. customthe solvent was removed under reduced pressure
  5. filtrationthe residue was purified by filtration through 1000 g of silica gel (hexane/methylene chloride 9:1)

Sources & evidence

ORD record
ord-5bffcb4a5552453c8b1c270be1b6f237
Source dataset
uspto-grants-2004_09
Patent number
US06787618B1

Reaction notes

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