Iodobenzene → 2-Phenyl-4,7-dimethyl-indene
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[C:13]1([C:5]2[CH2:4][C:3]3[C:7]([CH:6]=2)=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=3[CH3:1])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
20 ml of triethylamine, 2.88 g (20 mmole) of 4,7-dimethyl-indene, 4.08 g (20 mmole) of iodobenzene and 0.134 g (0.6 mmole) of Pd(OAc)2 were stirred under reflux for 12 h. After it all the triethylamine was removed under reduced pressure. The residue was treated with the mixture 50 ml of water and 50 ml of diethyl ether. Etherial layer was separated, washed twice with water, filtered and dried over Na2SO4. Ether was removed and some 20 ml of pentane were added to the reaction mixture. It was cooled down to −20° C. and product was crystallized as white crystals, which were filtered, washed with small portion of cold pentane and dried in vacuum. The yield of product was 38%.
Workup
- temperatureunder reflux for 12 h
- customAfter it all the triethylamine was removed under reduced pressure
- additionThe residue was treated with the mixture 50 ml of water and 50 ml of diethyl ether
- customEtherial layer was separated
- washwashed twice with water
- filtrationfiltered
- dry with materialdried over Na2SO4
- customEther was removed
- additionsome 20 ml of pentane were added to the reaction mixture
- customproduct was crystallized as white crystals, which
- filtrationwere filtered
- washwashed with small portion of cold pentane
- customdried in vacuum
Sources & evidence
- ORD record
- ord-ea5c51bd73e64cfaa8c1791fef77532a
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271411B1
Reaction notes
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