Sodium Carbonate → 5-Bromoindoline

HRID 1727529Notes

Reaction equation

HRID 1727529 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-7befd57a42fd42378ad65fae69a5ae81
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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