Azobisisobutyronitrile → HCID 68497857, compound

HRID 1176257Notes

Reaction equation

HRID 1176257 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:17][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:16]=1

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 68503596HCID 68503596, compound

Product 1

HCID 68497857HCID 68497857, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 25.0 g of methyl 2-(3-methoxypropoxy)-4-methylbenzoate, 18.4 g of N-bromosuccinimide, 1.65 g of 2,2′-azobis(2-methylpropionitrile) and 2.46 g of dibenzoyl peroxide in 1.2 l of carbon tetrachloride is heated to reflux with stirring and stirred over 3 hours (succinimide crystallizes out). The reaction mixture is cooled and clarified by filtration, and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.30 (1:1 EtOAc-heptane); Rt=17.10 (II).

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customcrystallizes out)
  4. temperatureThe reaction mixture is cooled
  5. filtrationclarified by filtration
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-f8bb009ff21e4d89bf3bab1e648a2e28
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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