Dichlorodiphenylsilane → (3-Bromophenyl)(dibenzo[b,d]thiophen-4-yl)diphenylsilane

HRID 1957896Notes

Reaction equation

HRID 1957896 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Li])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CCCCCC.BrC1C=CC=C(Br)C=1.Cl[Si:29](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH:43]1[C:51]2[C:50]3[CH:52]=[CH:53][CH:54]=[CH:55][C:49]=3[S:48][C:47]=2[C:46]([Li])=[CH:45][CH:44]=1>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([Si:29]([C:55]2[C:49]3[S:48][C:47]4[CH:46]=[CH:45][CH:44]=[CH:43][C:51]=4[C:50]=3[CH:52]=[CH:53][CH:54]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 6627DichlorodiphenylsilaneHCID 79271,3-DibromobenzeneHCID 8058HexaneHCID 178418339ButyllithiumHCID 178506665C12H7LiSHCID 178506674HCID 178506674, compound2×

Product 1

HCID 86676048(3-Bromophenyl)(dibenzo[b,d]thiophen-4-yl)diphenylsilaneYield 31%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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%).

Workup

  1. customThe resultant reaction solution
  2. customprepared
  3. additionabove was introduced dropwise
  4. customIt was quenched with water
  5. extractionextracted with ether
  6. dry with materialdried over Na2SO4
  7. customUpon evaporation of the solvent
  8. customthe residue was purified by column chromatography on silica gel with hexane/DCM (9/1

Sources & evidence

ORD record
ord-0ec4363bc7ac4eaba7772917abab45fe
Source dataset
uspto-grants-2013_04
Patent number
US08409729B2

Reaction notes

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