N-bromobutanimide → 5-Bromo-2-oxindole

HRID 17167Notes

Reaction equation

HRID 17167 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Br:11]N1C(=O)CCC1=O>C(#N)C>[Br:11][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 321710Oxindole

Product 1

HCID 6111935-Bromo-2-oxindoleYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1,3-dihydro-indol-2-one (1.3 g, 9.76 mmol) in acetonitrile (20 mL) at −5° C. was treated with N-bromosuccinimide, warmed to room temperature, stirred overnight and filtered to give 1.8 g (87% yield) of the desired product. MS (ESI(+)) m/e 209.9, 211.9 (M−H)−.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-0d6af9dc736d4364b96547b8d6772231
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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