تفاعل #2045080

معادلة التفاعل

1,3-dibromobenzene

n-butyllithium

hexane

dichlorodiphenylsilane

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

→

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

المردود 52.0%

المذيبات

ether

ether

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resultant reaction solution
2. 2
   أخرىprepared
3. 3
   workup.ADDITIONabove was introduced dropwise
4. 4
   أخرىwas quenched with water
5. 5
   استخلاصextracted with ether
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحUpon filtration and evaporation of the solvent
8. 8
   أخرىthe residue was purified by column chromatography on silica gel with hexane/DCM (9/1

الإجراء التجريبي

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.

المصدر