Azobisisobutyronitrile → 4-Bromomethyl-1-ethoxy-2-(3-methoxypropoxy)benzene

HRID 1176449Notes

Reaction equation

HRID 1176449 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH3:2].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 592240741-Ethoxy-2-(3-methoxypropoxy)-4-methylbenzene

Product 1

HCID 685032054-Bromomethyl-1-ethoxy-2-(3-methoxypropoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 2.01 g of 1-ethoxy-2-(3-methoxypropoxy)-4-methylbenzene, 1.76 g of N-bromosuccinimide and 0.150 g of 2,2′-azobis(2-methylpropionitrile) in 90 ml of carbon tetrachloride is kept at reflux with stirring over 1 hour. The reaction mixture is cooled and clarified by filtration, and the filtrate is concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is cooled
  3. filtrationclarified by filtration
  4. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-a1d154e1bad449b19a5896d374827723
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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