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

HRID 241501

Reaction equation

HRID 241501 reaction equation
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

Participants

9

Reactant 6

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

Product 2

HCID 86684651(3-Bromophenyl)diphenyl(triphenylen-2-yl)silaneYield 75%HCID 178506674HCID 178506674, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eb95efb52ae145e2abfbd0c227366ae9
Source dataset
uspto-grants-2014_02
Patent number
US08652656B2

Linked notes

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