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

HRID 902404

反応式

HRID 902404 の反応式
[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

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 682269,10-DibromoanthraceneHCID 178418306HCID 178418306、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-69 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1149d602c24b4fc49eafb64fecc366d4
出典データセット
uspto-grants-2008_04
特許番号
US07365198B2

関連ノート

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