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

HRID 2268780Notes

Reaction equation

HRID 2268780 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, 0.00695 mol) 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. 1H NMR (CDCl3) 1.39 (6H s), 6.8 (1H d), 7.3 (2H m), 7.9 (1H broad).

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-60d34022f8334928b263f79f25977196
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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