1,1',1''-(Chlorosilylidyne)tris(benzene) → (4-Bromophenyl)triphenylsilane

HRID 1893101Notes

Reaction equation

HRID 1893101 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Li]CCCC.Cl[Si:15]([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:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([Si:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 114141,2-DibromobenzeneHCID 178418339Butyllithium

Product 1

HCID 297506(4-Bromophenyl)triphenylsilaneYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

As depicted in Reaction 2, a solution of 4 g (17 mmol) of dibromobenzene in ether was cooled. To the solution were sequentially added n-BuLi and chlorotriphenylsilane. The mixture was allowed to react at room temperature. After completion of the reaction, the reaction mixture was extracted with ether. After the solvent was removed under reduced pressure, the residue was purified by column chromatography to give the title compound. The product was collected by filtration under reduced pressure and dried. Yield: 66%. 1H-NMR (CDCl3, ppm): 7.54-7.5 (m, Ar—H), 7.45 (Ar—H), 7.40-7.35 (m, Ar—H). IR (KBr, cm−1): 1568, 1477-1376, 1110, 810, 727, 698. MS (EI) (Calcd. for C24H19BrSi: 414. Found: 414).

Workup

  1. customAs depicted in Reaction 2
  2. customto react at room temperature
  3. customAfter completion of the reaction
  4. extractionthe reaction mixture was extracted with ether
  5. customAfter the solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-be85add13dc945dd9b0d62f386bf4271
Source dataset
uspto-grants-2013_08
Patent number
US08512877B2

Reaction notes

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