1,2-Dibromoethane → 1H-Indene, 3,3'-(1,2-ethanediyl)bis[4,7-dimethyl-

HRID 865317

Reaktionsgleichung

[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].C[C:18]1[CH:26]=[CH:25][C:24](C)=[C:23]2[C:19]=1[CH:20]=[CH:21][CH:22]2[Li].BrCCBr>O1CCCC1.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]([CH2:15][CH2:14][C:13]1[C:12]3[C:20](=[C:19]([CH3:23])[CH:18]=[CH:26][C:25]=3[CH3:24])[CH2:21][CH:22]=1)=[CH:5][CH2:6]2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

38.2 g (265 mmol) of 4,7-dimethylindene was dissolved in 350 ml of tetrahydrofuran and the solution was cooled to 0° C. Then 165 ml of n-butyllithium (1,6M in hexane, 264 mmol) was added dropwise over 2.5 hours. After warming to room temperature and stirring for 4 hours a purple solution of 4,7-dimethylindenyl-lithium was obtained. This solution was cooled to -70° C. and treated dropwise with 25,3 g of 1,2-dibromoethane (135 mmol) in 15 ml of tetrahydrofuran over 35 min. After warming to room temperature, a pale yellow solution was obtained, and then water was added. The organic phase was collected and dried over Na2SO4. The solvent was removed by vacuum evaporation to provide 20 g of crude product (48% yield).

Aufarbeitung

temperatureAfter warming to room temperature
customwas obtained
temperatureThis solution was cooled to -70° C.
temperatureAfter warming to room temperature
customa pale yellow solution was obtained
customThe organic phase was collected
dry with materialdried over Na2SO4
customThe solvent was removed by vacuum evaporation

Quellen und Nachweise

ORD-Eintrag: ord-d661a9859bd947ce97004226853d618c
Quelldatensatz: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05565533

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