Water → 3-Bromo-3-methyloxindole

Participants

Reaction Steps

N-Bromosuccinimide (NBS) (5.42 g, 30.49 mmol) was dissolved in cold THF (100 mL) The resulting THF solution was then added dropwise via addition funnel to a stirring solution of 3-methylindole LXXXIII (2.00 g, 15.25 mmol) in mixed t-BuOH (100 mL) and H2O (1 mL) at rt over a period of one hour. After stirred for an additional hour, the solution was concentrated under reduced pressure and the crude material was directly purified by silica gel column chromatography (EtOAc-hexanes 1:4) to give 3-bromo-3-methyl-2-indolinone as a pale yellow solid 3-bromo-3-methyl-2-indolinone LXXXIV (2.52 g, 73%).

Provenance & Evidence