N-bromobutanimide → 7-Bromo-5-fluoroindolin-2-one

HRID 2191407Notes

Reaction equation

HRID 2191407 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Br:12]N1C(=O)CCC1=O>C(#N)C>[Br:12][C:9]1[CH:10]=[C:2]([F:1])[CH:3]=[C:4]2[C:8]=1[NH:7][C:6](=[O:11])[CH2:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 534188887-Bromo-5-fluoroindolin-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Fluoro-1,3-dihydro-indol-2-one 4a (1.5 g, 0.01 mol) was dissolved in 15 ml of acetonitrile under stirring, and added dropwise with N-bromosuccinimide (1.8 g, 0.01 mol) at room temperature. Upon completion of the addition, the mixture was stirred overnight and lots of precipitate was formed. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered to obtain 7-bromo-5-fluoro-1,3-dihydro-indol-2-one 4b (2 g, yield 87%) as a gray solid.

Workup

  1. additionUpon completion of the addition
  2. stirringthe mixture was stirred overnight
  3. customlots of precipitate was formed
  4. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-d7abb58a09484e44a9a24c84cf603182
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

Loading…