反应 #2045080

反应方程式

1,3-dibromobenzene

n-butyllithium

hexane

dichlorodiphenylsilane

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

→

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

收率 52.0%

溶剂

ether

ether

反应条件

后处理

1. 1
   其他The resultant reaction solution
2. 2
   其他prepared
3. 3
   workup.ADDITIONabove was introduced dropwise
4. 4
   其他was quenched with water
5. 5
   萃取extracted with ether
6. 6
   干燥dried over Na2SO4
7. 7
   过滤Upon filtration and evaporation of the solvent
8. 8
   其他the residue was purified by column chromatography on silica gel with hexane/DCM (9/1

实验过程

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.

来源