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

HRID 964784Notes

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-ee7e385148994034b7cbf333d993d028
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770753

Reaction notes

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