Hydrochloric Acid → (5-Bromo-1,3-phenylene)bis(trimethylsilane)

HRID 842464

反応式

HRID 842464 の反応式
Br[C:2]1[CH:3]=[C:4]([Si:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.[Li]CCCC.[CH3:18][Si:19](Cl)([CH3:21])[CH3:20].Cl>CCOCC>[CH3:10][Si:9]([CH3:12])([CH3:11])[C:4]1[CH:5]=[C:6]([Br:8])[CH:7]=[C:2]([Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 6262443,5-Dibromo-1-trimethylsilylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 12884904(5-Bromo-1,3-phenylene)bis(trimethylsilane)収率 94%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-68 °C

実験手順

17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O—phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H).

後処理

  1. stirringThe solution was stirred overnight at room temperature
  2. stirringStirring for 30 minutes
  3. customresulted in two clear phases
  4. dry with materialEt2O—phase was dried with MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. distillationRaw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar

出典と根拠

ORDレコード
ord-ac451b3e7e7d440da596d8a5d4a7190e
出典データセット
uspto-grants-2002_04
特許番号
US06376409B1

関連ノート

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