Chlorotrimethylsilane → Silane, (10-bromo-9-anthracenyl)trimethyl-

HRID 902404

Reaction equation

HRID 902404 reaction equation
[Br:1][C:2]1[C:3]2[C:8]([C:9](Br)=[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])(C)(C)C.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[Br:1][C:2]1[C:3]2[C:8]([C:9]([Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 682269,10-DibromoanthraceneHCID 178418306HCID 178418306, compound

Product 1

HCID 616523Silane, (10-bromo-9-anthracenyl)trimethyl-Yield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-69 °C

Procedure

Under an argon atmosphere, the temperature of a solution of 9,10-dibromoanthracene (5 g, 15 mmol) in dry-THF (50 ml) was cooled to −69° C., and t-butyllithium (18 mmol) was dropped to the solution. After the mixture had been stirred for 3 hours, chlorotrimethylsilane (3 ml, 22.5 mmol) was added to the mixture, and the whole was stirred at −69° C. for an additional 3 hours. After the temperature of the resultant had been increased to room temperature, the resultant was quenched with sodium bicarbonate water, extracted with toluene, and dried with sodium sulfate. Then, the solvent was removed by distillation. The residue was dispersed and washed with hexane, the insoluble matter was removed, and the filtrate was condensed. The condensate was washed with ethanol, and was then subjected to silica gel column chromatography, whereby 1 g of 9-bromo-10-trimethylsilylanthracene was obtained.

Workup

  1. stirringthe whole was stirred at −69° C. for an additional 3 hours
  2. temperatureAfter the temperature of the resultant had been increased to room temperature
  3. customthe resultant was quenched with sodium bicarbonate water
  4. extractionextracted with toluene
  5. dry with materialdried with sodium sulfate
  6. customThen, the solvent was removed by distillation
  7. additionThe residue was dispersed
  8. washwashed with hexane
  9. customthe insoluble matter was removed
  10. customcondensed
  11. washThe condensate was washed with ethanol

Sources & evidence

ORD record
ord-1149d602c24b4fc49eafb64fecc366d4
Source dataset
uspto-grants-2008_04
Patent number
US07365198B2

Linked notes

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