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

HRID 2365026Notes

Reaction equation

HRID 2365026 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-957b5578a7f7461bb92081bc7222eb0a
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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