Acetic Acid → 4-(4-Bromo-phenyl)1,3-dihydro-indol-2-one

HRID 983009Notes

Reaction equation

HRID 983009 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:40])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:40])[NH:12]3)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21124087PyridiniumtribromideHCID 225619344-(4-Bromo-phenyl)-1H-indole

Product 1

HCID 225617214-(4-Bromo-phenyl)1,3-dihydro-indol-2-oneYield 88%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 86587657t-BuOH ethanol aceticacidSolvent

Conditions

Temperature
27 °C

Procedure

To the suspension of 4-(4-bromo-phenyl)-1H-indole (1.20 g, 4.41 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (54 mL) was added pyridinium tribromide (4.23 g, 13.23 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (30 mL). Zinc dust was added to the reaction mixture portionwise until the color changed from deep red to light yellow, and the reaction mixture was stirred at room temperature for one hour. The unreacted zinc dust was filtered off and washed with ethanol. The filtrate was concentrated, and the syrupy residue was suspended in water (300 mL) for 0.5 hour. The solid product was precipitated out, filtered, and washed repeatedly with water to remove the zinc salt and pyridine salt. After high vacuum dry, a pure product (1.12 g, 88%) was obtained.

Workup

  1. stirringwas stirred at room temperature for one hour
  2. filtrationThe unreacted zinc dust was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. waitthe syrupy residue was suspended in water (300 mL) for 0.5 hour
  6. customThe solid product was precipitated out
  7. filtrationfiltered
  8. washwashed repeatedly with water
  9. customto remove the zinc salt and pyridine salt
  10. customAfter high vacuum dry

Sources & evidence

ORD record
ord-c5b60e77e4f64c4887d153db1a0375f8
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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