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

HRID 905758Notes

Reaction equation

HRID 905758 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 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-fluoro-1,3-dihydro-indol-2-one (1.5 g, 10 mmol) in 15 ml of acetonitrile and N-bromosuccinimide (1.8 g, 10 mmol) was stirred at room temperature overnight until the precipitate was formed. The solid was filtered washed with ethanol (5 ml) and dried in vacuo to give 7-bromo-5-fluoro-1,3-dihydro-indol-2-one (1.6 g, 69.6%) as a white solid.

Workup

  1. customwas formed
  2. filtrationThe solid was filtered
  3. washwashed with ethanol (5 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-37f9eceecd654120add8f8e3f9c5c3b9
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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