Azobisisobutyronitrile → 6-Bromomethyl-1-(3-methoxypropyl)-3,3-dimethyl-1,3-dihydroindol-2-one

HRID 1176307Notes

Reaction equation

HRID 1176307 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=2)[C:8]([CH3:17])([CH3:16])[C:7]1=[O:18].[Br:19]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:19][CH2:15][C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:16])([CH3:17])[C:7](=[O:18])[N:6]2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 685021401-(3-Methoxypropyl)-3,3,6-trimethyl-1,3-dihydroindol-2-one

Product 1

HCID 685003296-Bromomethyl-1-(3-methoxypropyl)-3,3-dimethyl-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 1.08 g of 1-(3-methoxypropyl)-3,3,6-trimethyl-1,3-dihydroindol-2-one, 0.801 g of N-bromosuccinimide, 0.014 g of 2,2′-azobis(2-methylpropionitrile) and 0.021 g of dibenzoyl peroxide in 50 ml of carbon tetrachloride is heated to reflux with stirring. The reaction mixture is stirred at reflux over 1 hour (succinimide crystallizes out) and subsequently cooled to room temperature. The succinimide is filtered off 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=0.40 (dichloromethane-diethyl ether); Rt=17.22 (II).

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. stirringThe reaction mixture is stirred
  4. customcrystallizes out) and
  5. filtrationThe succinimide is filtered off
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-24b8c57af2f744b1afe36ba62ca4a75a
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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