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

HRID 1383808Notes

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

Conditions

Temperature: 60 °C

Procedure

90 cm3 (0.24 mol) of a 20% strength solution of butyllithium 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

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

Sources & evidence

ORD record: ord-9e2bb7b7fc40490eaa93eaa497d9d5a8
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255506B1

Reaction notes

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