Hydrogen Bromide → 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

HRID 1276316Notes

Reaction equation

HRID 1276316 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[Br:13]Br.Br>C(Cl)(Cl)Cl>[Br:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:11])[C:2]2([CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.12 g, 6.95 mmol) was dissolved in chloroform and stirred at room temperature under nitrogen. Bromine (1.12 g) was added and the mixture was heated under reflux until HBr evolution ceased and the bromine colour was discharged from the solution. The solution was washed with sodium metabisulphite solution and sodium hydrogen carbonate solution, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give 5-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. washThe solution was washed with sodium metabisulphite solution and sodium hydrogen carbonate solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto dry under reduced pressure

Sources & evidence

ORD record
ord-43363e9a469342a5add6fe26d9bf116c
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

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