Dichlorodiphenylsilane → (3-Bromophenyl)diphenyl(triphenylen-2-yl)silane

HRID 241501

반응식

HRID 241501 반응식
C([Li:5])CCC.CCCCCC.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.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.[C:35]1([Li])[C:52]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]=2[CH:38]=[CH:37][CH:36]=1.Cl[SiH](Cl)C1C=CC=CC=1>CCOCC>[Br:12][C:13]1[CH:14]=[C:15]([Li:5])[CH:16]=[CH:17][CH:18]=1.[Br:19][C:15]1[CH:14]=[C:13]([Si:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:36]2[CH:37]=[CH:38][C:39]3[C:40]4[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:46]4[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:52]=3[CH:35]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

9

반응물 6

HCID 6627DichlorodiphenylsilaneHCID 79271,3-DibromobenzeneHCID 8058HexaneHCID 74207Dichloro(phenyl)silaneHCID 178418339ButyllithiumHCID 178506667HCID 178506667, 화합물

생성물 2

HCID 86684651(3-Bromophenyl)diphenyl(triphenylen-2-yl)silane수율 75%HCID 178506674HCID 178506674, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

Into a suspension of 2-bromotriphenylene (7.28 g, 23.70 mmol) in ether (50 mL) was added n-butyllithium solution in hexane (14.81 mL, 23.70 mmol) dropwise at −78° C. The suspension was gradually warmed to 0° C. and stirred for 3 hours to yield a solution of triphenylenyllithium. In a separate flask a solution of 3-bromophenyllithium was prepared by dropwise addition of n-butyllithium solution in hexane (14.81 mL, 23.70 mmol) into a solution of 1,3-dibromobenzene (2.87 mL, 23.70 mmol) in ether (50 mL). The solution was stirred at this temperature for 2.5 hours before being transferred into a solution of dichlorodiphenylsilane (4.88 mL, 23.70 mmol) in ether (30 mL) at −78° C. After stirring for another 2 h, the triphenylenyllithium solution prepared above was introduced dropwise into the flask containing the dichlorophenylsilane. The reaction mixture was allowed to gradually warm to room temperature and was stirred overnight. The mixture was quenched with water and the organic phase was isolated. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (85/15, v/v) as eluent to yield (3-bromophenyl)diphenyl(triphenylen-2-yl)silane (8.5 g, 75%) as a white powder.

후처리

  1. stirringAfter stirring for another 2 h
  2. additionabove was introduced dropwise into the flask
  3. stirringwas stirred overnight
  4. customThe mixture was quenched with water
  5. customthe organic phase was isolated
  6. customUpon evaporation of the solvent
  7. customthe residue was purified by column chromatography on silica gel with hexane/DCM (85/15

출처 및 근거

ORD 기록
ord-eb95efb52ae145e2abfbd0c227366ae9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08652656B2

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