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

HRID 983005Notes

Reaction equation

HRID 983005 reaction equation
[F: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]>[F: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 225616864-(4-fluorophenyl)-1H-indole

Product 1

HCID 225618524-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-oneYield 98%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 86587657t-BuOH ethanol aceticacidSolvent

Conditions

Temperature
27 °C

Procedure

To the suspension of 4-(4-fluoro-phenyl)-1H-indole (2.28 g, 10.79 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (147 mL) was added pyridinium tribromide (90% purity from Aldrich, 11.51 g, 32.38 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (108 mL). Zinc dust (10.52 g, 162 mmol) was added to the reaction mixture portionwise, 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 for 4 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 (2.40 g, 98%) was obtained.

Workup

  1. stirringthe reaction mixture was 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 for 4 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-56e2ee5ebcb946d9aaf49ee0c01275a9
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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