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

HRID 842474ノート

反応式

HRID 842474 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-b6d6adb7758148b7b4f4276a68aeef52
出典データセット
uspto-grants-2002_04
特許番号
US06376411B1

反応ノート

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