Azobisisobutyronitrile → 2-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

HRID 561794Notes

Reaction equation

HRID 561794 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]=1[CH3:13].[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:3]1[CH:4]=[C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22467254HCID 22467254, compound

Product 1

HCID 591775552-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-chloro-4-(2-methoxyethoxy)-2-methylbenzene from the previous step (1 eq.) in carbon tetrachloride (0.02 M) was added N-bromosuccinimide (1 eq.) and a few crystals of AIBN (1.1 eq.). The resulting mixture was irradiated with sunlamp at reflux for 1 h. The insolubles were removed via filtration and the filtrate was concentrated in vacuo to furnish the title compound.

Workup

  1. customThe resulting mixture was irradiated with sunlamp
  2. temperatureat reflux for 1 h
  3. customThe insolubles were removed via filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5e9a531dabde4f8f95c5003ed456e315
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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