Reaction #2045078

Reaction equation

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

m-bromophenyl lithium

n-butyllithium

hexane

1,3-dibromobenzene

m-bromophenyl lithium

dichlorodiphenylsilane

→

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

Yield 31.0%

Solvents

ether

ether

Conditions

Workup

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

Procedure

In another flask was prepared a solution of m-bromophenyl lithium by addition of n-butyllithium solution in hexane (2.5 M, 9.48 mL, 23.70 mmol) into a solution of 1,3-dibromobenzene (2.56 mL, 21.20 mmol) in ether (70 mL) at −78° C. followed by stirring at this temperature for 3.5 h. This m-bromophenyl lithium solution was added dropwise into a solution of dichlorodiphenylsilane (4.88 mL, 23.70 mmol) in ether (70 mL) at −78° C. The resultant reaction solution was stirred at this temperature for 2 h before the dibenzo[b,d]thiophen-4-yl lithium solution prepared above was introduced dropwise. The resultant solution was allowed to slowly warm to room temperature overnight. It was quenched with water, extracted with ether and dried over Na2SO4. Upon 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]thiophen-4-yl)diphenylsilane as a white powder (3.84 g, 31%).

Source