1,1-Dibromoethane → 1,2-Bis(2-methyl-4-phenylindenyl)ethane

HRID 356839Notes

Reaction equation

HRID 356839 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH:23](Br)[CH3:24]>C1(C)C=CC=CC=1.C1COCC1>[CH3:4][C:3]1[CH:21]([CH2:23][CH2:24][CH:15]2[C:14]3[C:9](=[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:11]=[CH:12][CH:13]=3)[CH:8]=[C:7]2[CH3:6])[C:20]2[C:1]([CH:2]=1)=[C:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1)[CH:17]=[CH:18][CH:19]=2

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 42924022-Methyl-7-phenylindeneHCID 178418339Butyllithium

Product 1

HCID 229949181,2-Bis(2-methyl-4-phenylindenyl)ethaneYield 5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

90 cm3 (0.24 mol) of a 20 % strength solution of butyl-lithium in toluene were added at room temperature under argon to a solution of 50 g (0.24 mol) of 3 in 500 ml of THF. The mixture was stirred at 60° C. for 2 hours, and cooled to -78° C., 22.5 g (0.12 mol) of dibromoethane were added, and the mixture was warmed to room temperature over the course of 18 hours. The reaction mixture was washed with 50 cm3 of H2O, the solvent was removed in vacuo, and the residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1), giving 2.5 g (5%) of 32 as a yellow oil which solidified slowly at -20° C.

Workup

  1. temperaturecooled to -78° C.
  2. temperaturethe mixture was warmed to room temperature over the course of 18 hours
  3. washThe reaction mixture was washed with 50 cm3 of H2O
  4. customthe solvent was removed in vacuo
  5. customthe residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1)

Sources & evidence

ORD record
ord-0c3bb6c53b7a4af7af0de8fa1576f129
Source dataset
uspto-grants-1998_11
Patent number
US05840644

Reaction notes

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