Chlorotrimethylsilane → 9,9-Dimethyl-9-silafluorene

HRID 1945367Notes

Reaction equation

HRID 1945367 reaction equation
Br[C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1Br.Cl[Si:16](C)([CH3:18])[CH3:17]>C1COCC1>[CH3:17][Si:16]1([CH3:18])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 69813054HCID 69813054, compound

Product 1

HCID 1395449,9-Dimethyl-9-silafluoreneYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2-Dibromobiphenyl (10 g, 1 eq, 0.032 mol) was placed in a flask, and THF (150 ml) was added thereto. Then, n-buthyllithium (24.1 ml, 1.2 eq, 0.038 mol) was gradually added at −78° C., the reaction mixture was stirred for 30 minutes, and chlorotrimethylsilane (4.1 g, 1.2 eq, 0.038 mol) was added thereto. The resultant solution was stirred for four hours and distilled water was added thereto, followed by stirring for about 10 minutes. The reaction solution was extracted with hexane, dried to remove the solvent and purified by column chromatography to give 5,5-dimethyl-5H-dibenzo[b,d]silole (5.17 g, yield=77%).

Workup

  1. additionThen, n-buthyllithium (24.1 ml, 1.2 eq, 0.038 mol) was gradually added at −78° C.
  2. distillationdistilled water
  3. additionwas added
  4. stirringby stirring for about 10 minutes
  5. extractionThe reaction solution was extracted with hexane
  6. customdried
  7. customto remove the solvent
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-ad9a35ccdd544d1da28ec2aa3e9dea38
Source dataset
uspto-grants-2013_03
Patent number
US08395144B2

Reaction notes

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