bis(4-broMophenyl)-diphenyl-silane synthesis
- Product Name:bis(4-broMophenyl)-diphenyl-silane
- CAS Number:18733-91-0
- Molecular formula:C24H18Br2Si
- Molecular Weight:494.29
106-37-6
80-10-4
18733-91-0
a) Under a dry nitrogen atmosphere, 10.81 g (50 mmol) of 1,4-dibromobenzene was dissolved in 400 mL of anhydrous tetrahydrofuran (THF) and the solution was cooled to -78 °C. Subsequently, 20 mL (50 mmol) of hexane solution of n-butyllithium (n-BuLi) was slowly added dropwise, keeping the reaction temperature at -78 °C. After the dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 1 hour. Then, 6.3 g (25 mmol) of diphenyl dichlorosilane dissolved in 80 mL of anhydrous THF was slowly added dropwise, and upon completion of the dropwise addition, the reaction mixture was allowed to slowly warm to room temperature and stirred overnight. After completion of the reaction, the solvent was evaporated to dryness using a rotary evaporator and the crude product obtained was purified by recrystallization from toluene. Ultimately, 10 g (0.021 mol) of bis(4-bromophenyl)diphenylsilane was obtained from recrystallization from n-butanol in 81% yield.
Yield: 96%
Reaction Conditions:
Stage #1:1.4-dibromobenzene with n-butyllithium in tetrahydrofuran at -78; for 2 h;Inert atmosphere;
Stage #2:diphenylsilyl dichloride in tetrahydrofuran at -78 - 20; for 14 h;Inert atmosphere;
Steps:
I Synthesis of Core 1-5-1
1,4-Dibromobenzene (10 g, 42.4 mmol) into a THF (100 ml) in a nitrogen stream -78°C From 2.5M n-BuLi (16.9 ml, 42.4 mmol) slowly into the stirring for 2 hours now and, at -78°C dichlorodiphenylsilane (4.9 g, 19.3 mmol) slowly into the stirring for 2 hours at room temperature after 12 hours stirring. EA and extracted with waterBack, and then dried over MgSO4, and concentrated to the resulting organic ilicagel column and recrystallization to give the desired compound 9.2 g (96%).
References:
DukSan Neolux Co. Lts.;Park, Bo-Ra;Jeong, Hwa-Sun;Jang, Jae-Wan;Song, HyeonJu;Park, Jeong-Hwan;Lee, Sun-hee;Kwon, Jae-Taek;Lee, Beom-Seong KR2016/69021, 2016, A Location in patent:Paragraph 0191-0193
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