1,2-Dibromoethane → HCID 18475060, compound

HRID 863737Notes

Reaction equation

HRID 863737 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].Br[CH2:23][CH2:24]Br>O1CCCC1.O>[CH3:1][C:2]1[CH:10]([CH:19]([CH:18]2[C:17]3[C:14](=[CH:15][CH:16]=[CH:23][CH:24]=3)[CH:13]=[C:12]2[CH3:11])[CH3:20])[C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 8058HexaneHCID 165871H-Indene, 2-methyl-HCID 178418339Butyllithium

Product 1

HCID 18475060HCID 18475060, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 500-ml glass reaction vessel, 4.3 g (33 mmol) of 2-methylindene was dissolved in 80 ml of tetrahydrofuran. 21 ml of a 1.6 M hexane solution of n-butyllithium was slowly added dropwise to the reaction vessel while cooling. The mixture was stirred at temperature for one hour, and then cooled again. To this mixture, 3.1 g of 1,2-dibromoethane was slowly added dropwise, and the resulting mixture was stirred at room tmperataure for 12 hours. 50 ml of water was added to the mixture, and the organic phase was fractionated. After drying, the organic phase was washed several times with heptane, and dried to give 2.9 g of bis-(2-methylindenyl)ethane.

Workup

  1. temperaturewhile cooling
  2. temperaturecooled again
  3. stirringthe resulting mixture was stirred at room tmperataure for 12 hours
  4. customAfter drying
  5. washthe organic phase was washed several times with heptane
  6. customdried

Sources & evidence

ORD record
ord-3bc2318aa331453282a76430419d666c
Source dataset
uspto-grants-1996_10
Patent number
US05561093

Reaction notes

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