Dichlorodiphenylsilane → HCID 86676049, compound

HRID 1957898Notes

Reaction equation

HRID 1957898 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.CCCCCC.Cl[Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:35]1[C:43]2[C:42]3[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=3[O:40][C:39]=2[C:38]([Li])=[CH:37][CH:36]=1>CCOCC>[Br:8][C:4]1[CH:3]=[C:2]([Si:21]([C:47]2[C:41]3[O:40][C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:43]=4[C:42]=3[CH:44]=[CH:45][CH:46]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 6627DichlorodiphenylsilaneHCID 79271,3-DibromobenzeneHCID 8058HexaneHCID 178418339ButyllithiumHCID 178506663HCID 178506663, compound

Product 1

HCID 86676049HCID 86676049, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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.

Workup

  1. customThe resultant reaction solution
  2. customprepared
  3. additionabove was introduced dropwise
  4. customwas quenched with water
  5. extractionextracted with ether
  6. dry with materialdried over Na2SO4
  7. filtrationUpon filtration and 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-d83ceacc711543829fe6d3609612740c
Source dataset
uspto-grants-2013_04
Patent number
US08409729B2

Reaction notes

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