Indene → 2-Phenyl-1H-indene

HRID 650298Notes

Reaction equation

HRID 650298 reaction equation
C(N(CC)CC)C.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C>[C:18]1([C:9]2[CH2:10][C:11]3[C:16]([CH:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7219IndeneHCID 8471TriethylamineHCID 11575Iodobenzene

Product 1

HCID 3534352-Phenyl-1H-indeneYield 46%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Procedure

20 ml of triethylamine, 2.2 g (20 mmole) of indene, 4.08 g (20 mmole) of iodobenzene and 0.134 g (0.6 mmole) of Pd(OAc)2 were stirred under reflux for 10 h. After that the mixture was cooled to room temperature and treated with 100 ml of ethanol. The crystalline precipitate was isolated, washed with ethanol and dried under vacuum to obtain 1.6 g (46%) of 2-phenyl-indene.

Workup

  1. temperatureunder reflux for 10 h
  2. customThe crystalline precipitate was isolated
  3. washwashed with ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c0f293e9c3094e1b89cb56df83fb9604
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

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