1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 58926930, compound

HRID 713588Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.C([Li])CCC.CCCCCC.Cl[Si:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)C>[Br:9][C:4]1[CH:3]=[C:2]([Si:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:7]=[C:6]([Br:8])[CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Into a solution of 1,3,5-tribromobenzene (9.0 g, 28.6 mmol) in diethyl ether (200 mL) was added n-butyllithium solution in hexane (2.5 M, 12 mL, 30.6 mmol) dropwise at −78° C. The reaction was stirred at this temperature for 30 minutes before a solution of chlorotriphenylsilane (9.27 g, 31.4 mmol) in diethyl ether (90 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 hour, and then allowed to warm to room temperature and continue to stir overnight, and finally refluxed for 2 hours. After cooling to room temperature, the solid was filtered off. 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 (3,5-dibromophenyl)triphenylsilane (4.0 g, 28%) as a white solid.

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringto stir overnight
temperaturefinally refluxed for 2 hours
temperatureAfter cooling to room temperature
filtrationthe solid was filtered off
customUpon evaporation of the solvent
customthe residue was purified by column chromatography on silica gel with hexane/DCM (9/1

Sources & evidence

ORD record: ord-73985adb7d1f4b6c9b5859dc6e5dc143
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09184399B2

Reaction notes

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