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

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Reaction Steps

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).

Provenance & Evidence