Azobisisobutyronitrile → 7-Bromomethyl-3,3-dimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one

HRID 1712519Notes

Reaction equation

HRID 1712519 reaction equation
[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:3]1=[O:20].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[C:3](=[O:20])[C:2]2([CH3:21])[CH3:1]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 685015123,3,7-Trimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one

Product 1

HCID 684977467-Bromomethyl-3,3-dimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 3.10 g of 3,3,7-trimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one, 1.86 g of N-bromosuccinimide, 0.050 g of dibenzoyl peroxide and 0.033 g of 2,2′-azobis(2-methylpropionitrile) in 100 ml of carbon tetrachloride is kept at reflux with stirring over 2 hours. 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). Rf=0.42 (1:10 EtOAc-heptane); Rt=26.45 (II).

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-2e35cdd313784f0ca8de196275a54a19
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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