2,3-Dibromopropene → 2-Bromo-8-(phenyldimethylsilyl)-oct-1-ene

HRID 1265973ノート

反応式

HRID 1265973 の反応式
[CH2-:1][CH2:2][CH2:3][CH2:4][CH2-:5].[Mg+2].[Mg+2].[Br-:8].[Br-].[C:10]1([Si:16]([CH3:19])([CH3:18])Cl)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[C:21]([CH2:23]Br)=[CH2:22]>C1COCC1>[Br:8][C:2]([CH2:3][CH2:4][CH2:5][CH2:22][CH2:21][CH2:23][Si:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:19])[CH3:18])=[CH2:1]

参加物

5

反応物 3

HCID 105522,3-DibromopropeneHCID 13029ChlorodimethylphenylsilaneHCID 3637391Pentamethylene-1,5-bis(magnesium bromide)

生成物 1

HCID 185482212-Bromo-8-(phenyldimethylsilyl)-oct-1-ene収率 24.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

Commercially available pentamethylenebis(magnesium bromide) (37 ml, 0.5 M in THF, 18.5 mmol) was cooled in an ice bath. A solution of 3.16 g (18.5 mmol) of phenyldimethylchlorosilane in roughly 7 ml of THF was added. The reaction mixture was stirred at 5° C. for 15 minutes then at room temperature for 35 minutes, then recooled to 5° C. 2,3-Dibromopropene (3.7 g, 18.5 mmol) in roughly 5 ml of THF was added to the reaction mixture, which was held at 5° C. for 5 minutes, then warmed to room temperature and stirred overnight. The reaction mixture was quenched with water. Ether and a small amount of IN HCl was added. The phases were separated, and the organic phase was washed with water and brine, dried over magnesium chloride and stripped. Column chromatography gave 1.47 g of 2-bromo-8-(phenyldimethylsilyl)-oct-1-ene as a colorless oil.

後処理

  1. waitat room temperature for 35 minutes
  2. customrecooled to 5° C
  3. waitwas held at 5° C. for 5 minutes
  4. temperaturewarmed to room temperature
  5. stirringstirred overnight
  6. customThe reaction mixture was quenched with water
  7. additionEther and a small amount of IN HCl was added
  8. customThe phases were separated
  9. washthe organic phase was washed with water and brine
  10. dry with materialdried over magnesium chloride

出典と根拠

ORDレコード
ord-f0997c82c182474089ce2c00a79a0268
出典データセット
uspto-grants-2003_04
特許番号
US06548448B2

反応ノート

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