Bromine → 1-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 2290181Notes

Reaction equation

HRID 2290181 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:13]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 24408BromineHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 23665763Sodium Bisulfite

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To N-acetylindoline, 116.6 g (0.724 mol) in a 1000 ml 3 neck flash fitted with overhead stirrer, thermometer and gas inlet (to a sodium hydroxide trap) in 150 ml acetic acid was added bromine, 32.25 ml (0.68 mol) over a period of 30 minutes. The mixture was kept at 30° C. with ice bath cooling. When addition was complete, the yellow suspension was slowly poured into one liter of ice water and solid sodium bisulfite was added to destroy any residual bromine. The resulting slightly off white solid was filtered and washed several times with water and allowed to dry overnight. The resulting solid was recrystallized from 800 ml of methanol to give 122.86 g (70.7% by weight yield) of 5-bromo-N-acetylindoline.

Workup

  1. customThe mixture was kept at 30° C. with ice bath
  2. temperaturecooling
  3. additionWhen addition
  4. additionwas added
  5. customto destroy any residual bromine
  6. filtrationThe resulting slightly off white solid was filtered
  7. washwashed several times with water
  8. customto dry overnight
  9. customThe resulting solid was recrystallized from 800 ml of methanol

Sources & evidence

ORD record
ord-9719e96af27c471c8619889b0ae00a6f
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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