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

HRID 2068739Notes

Reaction equation

HRID 2068739 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 86,943.703%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Fluoro-1,3-dihydro-indol-2-one 12a (1.5 g, 0.01 mmol) was dissolved in 15 mL of acetonitrile under stirring at room temperature, and N-bromosuccinimide (1.8 g, 0.01 mmol) was then added dropwise to the solution. Upon completion of the addition, the reaction mixture was stirred overnight and lots of precipitates were formed. The reaction was completed until TLC showed the disappearance of starting materials, and the reaction mixture was filtered to give 7-bromo-5-fluoro-1,3-dihydro-indol-2-one 12b (2 g, 87%) as a gray solid.

Workup

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

Sources & evidence

ORD record
ord-c8c663b927904c3fa7430db7bed53e30
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

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