Indole → 1-Phenyl-1H-indole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(=O)(O)[O-].[K+]>BrC1C=CC=CC=1.[Cu]I>[C:4]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
5
Procedure
A suspension of indole (8.2 g), potassium bicarbonate (12 g) and copper (I) iodide (2.7 g) in bromobenzene (70 mL) was refluxed for 3 hours under nitrogen atmosphere. To the mixture copper (I) iodide (11 g) was added and the mixture was refluxed for additional 6 hours. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1 to 20:1) to provide 8.4 g of the title compound. Yield 62%.
Workup
- temperaturewas refluxed for 3 hours under nitrogen atmosphere
- temperaturethe mixture was refluxed for additional 6 hours
- customThe insoluble material was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1 to 20:1)
Sources & evidence
- ORD record
- ord-df943a1910d34487b1cad511b5518662
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172085B2
Reaction notes
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