Реакция #2045080

Уравнение реакции

1,3-dibromobenzene

n-butyllithium

hexane

dichlorodiphenylsilane

dibenzo[b,d]furan-4-yl lithium

→

(3-bromophenyl)(dibenzo[b,d]furan-4-yl)diphenylsilane

Выход 52.0%

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   ДругоеThe resultant reaction solution
2. 2
   Другоеprepared
3. 3
   workup.ADDITIONabove was introduced dropwise
4. 4
   Другоеwas quenched with water
5. 5
   Экстракцияextracted with ether
6. 6
   Сушкаdried over Na2SO4
7. 7
   ФильтрацияUpon filtration and evaporation of the solvent
8. 8
   Другоеthe residue was purified by column chromatography on silica gel with hexane/DCM (9/1

Методика

Into a solution of dibenzo[b,d]furan (4.98 g, 29.6 mmol) in ether (50 mL) at −78° C. was added n-butyllithium solution in hexane (2.5 M, 9.48 mL, 23.70 mmol) dropwise and the solution was allowed to warm to room temperature and stirred for 20 h to yield a dibenzo[b,d]furan-4-yl lithium solution. Into a solution of 1,3-dibromobenzene (2.56 mL, 21.20 mmol) in ether (50 mL) was added n-butyllithium solution in hexane (2.5 M, 9.48 mL, 23.70 mmol) dropwise at −78° C. The reaction solution was stirred at this temperature for 3.5 h before adding into a solution of dichlorodiphenylsilane (4.88 mL, 23.70 mmol) in ether (50.0 mL) at −78° C. The resultant reaction solution was stirred at this temperature for 2 h before the dibenzo[b,d]furan-4-yl lithium solution prepared above was introduced dropwise. The reaction mixture was allowed to slowly warm to room temperature overnight at which time it was quenched with water, extracted with ether, and dried over Na2SO4. Upon filtration and evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (9/1, v/v) as eluent to yield (3-bromophenyl)(dibenzo[b,d]furan-4-yl)diphenylsilane (6.2 g, 52%) as a white powder.

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