Benzoyl Peroxide → HCID 67414524, compound

HRID 220613Notes

Reaction equation

HRID 220613 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH3:16])=[O:5].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][Br:24])=[O:5]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67414804HCID 67414804, compound

Product 1

HCID 67414524HCID 67414524, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.30 g (0.9 mmol) of 5-chloro-7-methyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in CCl4 (10 ml), 016 g N-bromosuccinimide (NBS) and 11 mg of benzoyl peroxide were added. The reaction mixture was heated at reflux for one hour and cooled down to RT. The succinimide was filtered off and the solvent removed under reduced pressure to afford 0.35 g (95%) of 7-bromomethyl-5-chloro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester as a light brown solid. This product was directly used in the next step (unstable).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. filtrationThe succinimide was filtered off
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e3488531582844789d137ad92b38313d
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

Loading…