Reaktion #2369980

Reaktionsgleichung

triphenylenyllithium

dichlorophenylsilane

dichlorodiphenylsilane

n-butyllithium

hexane

1,3-dibromobenzene

→

3-bromophenyllithium

(3-bromophenyl)diphenyl(triphenylen-2-yl)silane

Ausbeute 75.0%

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for another 2 h
2. 2
   workup.ADDITIONabove was introduced dropwise into the flask
3. 3
   workup.STIRRINGwas stirred overnight
4. 4
   SonstigeThe mixture was quenched with water
5. 5
   Sonstigethe organic phase was isolated
6. 6
   SonstigeUpon evaporation of the solvent
7. 7
   Sonstigethe residue was purified by column chromatography on silica gel with hexane/DCM (85/15

Vorschrift

Into a suspension of 2-bromotriphenylene (7.28 g, 23.70 mmol) in ether (50 mL) was added n-butyllithium solution in hexane (14.81 mL, 23.70 mmol) dropwise at −78° C. The suspension was gradually warmed to 0° C. and stirred for 3 hours to yield a solution of triphenylenyllithium. In a separate flask a solution of 3-bromophenyllithium was prepared by dropwise addition of n-butyllithium solution in hexane (14.81 mL, 23.70 mmol) into a solution of 1,3-dibromobenzene (2.87 mL, 23.70 mmol) in ether (50 mL). The solution was stirred at this temperature for 2.5 hours before being transferred into a solution of dichlorodiphenylsilane (4.88 mL, 23.70 mmol) in ether (30 mL) at −78° C. After stirring for another 2 h, the triphenylenyllithium solution prepared above was introduced dropwise into the flask containing the dichlorophenylsilane. The reaction mixture was allowed to gradually warm to room temperature and was stirred overnight. The mixture was quenched with water and the organic phase was isolated. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (85/15, v/v) as eluent to yield (3-bromophenyl)diphenyl(triphenylen-2-yl)silane (8.5 g, 75%) as a white powder.

Quelle