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

HRID 1712458Notes

Reaction equation

HRID 1712458 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-f0b07423564843f2b5cce0a732416966
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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