Sodium Carbonate → 5-Bromoindoline

HRID 423787Notes

Reaction equation

HRID 423787 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(=O)C)[CH2:6][CH2:5]2.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 34115665-BromoindolineYield 55%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of crude 1-(5-bromo-2,3-dihydro-indol-1-yl)-ethanone (100 g, 0.34 mol) in HCl (20%, 1200 mL) was heated at reflux for 6 h. The mixture was basified with Na2CO3 to pH 8.5-10 and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-bromo-2,3-dihydro-1H-indole (37 g, 55%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0a65769917c4ec2a83133e95f0cd488
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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