1,1',1''-(Chlorosilylidyne)tris(benzene) → 9-Bromo-l0-triphenysilyl anthracene

HRID 270735

Reaction equation

HRID 270735 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([Br:16])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.C([Li])CCC.[C:22]1([Si:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[Br:16][C:9]1[C:10]2[C:15]([C:2]([Si:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:3]3[C:8]=1[CH:7]=[CH:6][CH:5]=[CH:4]3)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 682269,10-DibromoanthraceneHCID 178418339Butyllithium

Product 1

HCID 598339599-Bromo-l0-triphenysilyl anthracene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, 12 g (35.7 mmol) of 9,10-dibromoanthracene, and 300 ml of tetrahydrofuran (THF) were added to a round-bottom flask. Next, 14.4 ml (35.7 mmol, 2.5M) of n-butyl lithium was added dropwise slowly into the round-bottom flask at −78° C. After mixing and reacting for 30 min, 12 g (40.7 mmol) triphenylsilyl chloride with 50 ml THF were added dropwise slowly into the round-bottom flask at −78° C. After reacting at room temperature for 24 hours, the resulting mixture was subjected to extraction with a mixed solvent (ethyl acetate:H2O), dried over anhydrous MgSO4, filtered, and condensed, then the crude product was purified by column chromatography (n-hexane/acetyl acetate=15/1), A 9.0 g of pure 9-bromo-10-triphenysilyl anthracene was collected.

Workup

  1. additionAfter mixing
  2. waitAfter reacting at room temperature for 24 hours
  3. extractionthe resulting mixture was subjected to extraction with a mixed solvent (ethyl acetate:H2O)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customcondensed
  7. customthe crude product was purified by column chromatography (n-hexane/acetyl acetate=15/1)
  8. customA 9.0 g of pure 9-bromo-10-triphenysilyl anthracene was collected

Sources & evidence

ORD record
ord-fecb7ac6bffa4b2094f2007780da8def
Source dataset
uspto-grants-2008_11
Patent number
US07449593B2

Linked notes

Loading…