Reaction #2045080

Reaction equation

1,3-dibromobenzene

n-butyllithium

hexane

dichlorodiphenylsilane

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

→

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

Yield 52.0%

Solvents

ether

ether

Conditions

Workup

1. 1
   OtherThe resultant reaction solution
2. 2
   Otherprepared
3. 3
   workup.ADDITIONabove was introduced dropwise
4. 4
   Otherwas quenched with water
5. 5
   Extractionextracted with ether
6. 6
   Dryingdried over Na2SO4
7. 7
   FiltrationUpon filtration and evaporation of the solvent
8. 8
   Otherthe residue was purified by column chromatography on silica gel with hexane/DCM (9/1

Procedure

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.

Source