N-bromobutanimide → 5-Bromo-2-oxindole

HRID 24391Notes

Reaction equation

HRID 24391 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 91.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Oxindole (1.3 g) in 20 ml of acetonitrile was cooled to −10° C. and 2.0 g of N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at −10° C. and then 2 hours at 0° C. The precipitate which formed was collected, washed with water and dried to give 1.9 g (90% yield) of 5-bromo-2-oxindole.

Workup

  1. stirringThe reaction was stirred for 1 hour at −10° C.
  2. custom2 hours
  3. customat 0° C
  4. customThe precipitate which formed
  5. customwas collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-67febabef2914be4a3883a53898929f1
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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