Reaktion #2503589

Reaktionsgleichung

tetrakis(4-bromophenyl)silane

styrene

K2CO3

→

Tetrastilbenylsilane

Ausbeute 52.0%

Lösungsmittel

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA round bottom flask (50 mL) equipped with a teflon coated stir bar
2. 2
   SonstigeThe flask was fitted with a rubber septum
3. 3
   Sonstigepurged with nitrogen
4. 4
   Temperaturto cool to room temperature
5. 5
   workup.ADDITIONdiluted with CH2Cl2
6. 6
   Waschenwashed five times with brine
7. 7
   TrocknenThe organic phase was dried with MgSO4
8. 8
   Filtrationfiltered through silica gel
9. 9
   Sonstigethe solvent was evaporated under reduced pressure
10. 10
    workup.DISSOLUTIONThe residue was dissolved in CHCl3
11. 11
    Sonstigeprecipitated with hexanes
12. 12
    SonstigeThe colorless needle-like crystals were collected (52% yield)

Vorschrift

A round bottom flask (50 mL) equipped with a teflon coated stir bar was charged with tetrakis(4-bromophenyl)silane (326 mg, 0.5 mmol), styrene (2.0 g, 12 mmol), Pd(OAc)2 (14 mg, 12 mol %), K2CO3 (690 mg, 5 mmol), n-Bu4NBr (645 mg, 2 mmol), and DMA (10 mL). The flask was fitted with a rubber septum and purged with nitrogen prior to heating (80° C.) with stirring for 48 hours. The reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2, and washed five times with brine. The organic phase was dried with MgSO4, filtered through silica gel and the solvent was evaporated under reduced pressure. The residue was dissolved in CHCl3 and precipitated with hexanes. The colorless needle-like crystals were collected (52% yield). 1H NMR (CDCl3): δ 7.61 (d, J=8.0 Hz, 8H), 7.55 (m, 16H), 7.38 (t, J=7.3 Hz, J=8.0 Hz, 8H), 7.29 (t, J=7.3 Hz, 4H), 7.17 (AA′BB′ pattern, J=16.4 Hz, 8H). 13C NMR (CDCl3) δ 138.5, 137.1, 136.7, 133.4, 129.5, 128.6, 128.4, 127.7,126.5, 125.9.

Quelle