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

HRID 1957896노트

반응식

HRID 1957896 반응식
[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

참가 물질

8

반응물 6

HCID 6627DichlorodiphenylsilaneHCID 79271,3-DibromobenzeneHCID 8058HexaneHCID 178418339ButyllithiumHCID 178506665CID 101372253HCID 178506674HCID 178506674, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0ec4363bc7ac4eaba7772917abab45fe
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08409729B2

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