Water → 3-Bromo-3-methyloxindole

HRID 1951747Notes

Reaction equation

HRID 1951747 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.[OH2:19]>C1COCC1.CC(O)(C)C>[Br:1][C:10]1([CH3:9])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 6736SkatoleHCID 67184N-bromobutanimide

Product 1

HCID 217664783-Bromo-3-methyloxindole

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customthe crude material was directly purified by silica gel column chromatography (EtOAc-hexanes 1:4)

Sources & evidence

ORD record
ord-f5167fb71ce446ad88bf6d8f14276752
Source dataset
uspto-grants-2013_03
Patent number
US08404738B2

Reaction notes

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