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

HRID 1811229Notes

Reaction equation

HRID 1811229 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-9f146c1f5f30484ebdab1830f11bcf83
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

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