Water → alpha,alpha'-Bis(1-indenyl)-o-xylene

HRID 1290612Notes

Reaction equation

HRID 1290612 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][C:12]1[C:13]([CH2:18]Br)=[CH:14][CH:15]=[CH:16][CH:17]=1.O.Br[C:22]1[C:23](Br)=[C:24]([CH3:29])[C:25]([CH3:28])=[CH:26][CH:27]=1.[CH3:31]CCCCC>O1CCCC1>[CH:1]1([CH2:11][C:12]2[C:13]([CH2:18][CH:28]3[C:25]4[C:24](=[CH:23][CH:22]=[CH:27][CH:26]=4)[CH:29]=[CH:31]3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 962WaterHCID 7219IndeneHCID 8058HexaneHCID 343431,2-Dibromo-3,4-dimethylbenzeneHCID 66665o-Bis(bromomethyl)benzene

Product 1

HCID 15824690alpha,alpha'-Bis(1-indenyl)-o-xyleneYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

70 ml (0.175 moles) of lithium butyl 2.5M in hexane are added, over a period of about 20 minutes, to a solution of 25 g (0.215 moles) of indene in 100 ml of tetrahydrofuran. The mixture is left under stirring for 2 hours, and is then cooled to -10° C. 20 g (0.076 moles) of α,α'-dibromo-o-xylene dissolved in 100 ml of THF are then added, in about 1 hour, so that the temperature of the reaction mixture does not exceed -5° C. At the end, the temperature is left to rise to room temperature, the mixture is hydrolyzed with water and extracted with ethyl ether. The ether extracts, after washing until neutral, and drying on anhydrous sodium sulfate, are evaporated. The residue obtained is purified on a silica gel column using petroleum ether containing 1% of ethyl acetate as eluant. After evaporation of the eluant, 9.5 g of α,α'-bis(1-indenyl)-o-xylene, are obtained, characterized by 1H-NMR analysis, with a yield of 26% with respect to the starting dibromo-o-xylene.

Workup

  1. waitThe mixture is left
  2. additionare then added, in about 1 hour, so that the temperature of the reaction mixture
  3. customdoes not exceed -5° C
  4. waitAt the end, the temperature is left
  5. customto rise to room temperature
  6. extractionextracted with ethyl ether
  7. washafter washing until neutral, and
  8. dry with materialdrying on anhydrous sodium sulfate
  9. customare evaporated
  10. customThe residue obtained
  11. customis purified on a silica gel column
  12. customAfter evaporation of the eluant, 9.5 g of α,α'-bis(1-indenyl)-o-xylene
  13. customare obtained

Sources & evidence

ORD record
ord-e9be4b32533a40dfb33d7b03bb098828
Source dataset
uspto-grants-1998_05
Patent number
US05753578

Reaction notes

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