2,4-Dichloro-1-(2,2-dibromovinyl)benzene → 2,4-Dichloro-1-ethynylbenzene

HRID 275689ノート

反応式

HRID 275689 の反応式
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].C([Li])CCC>C1COCC1>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:3]#[CH:2]

参加物

4

反応物 2

HCID 120184412,4-Dichloro-1-(2,2-dibromovinyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 126397532,4-Dichloro-1-ethynylbenzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 1,1-dibromo-2-(2,4-dichlorophenyl)ethene (14 g, 42.4 mmol) in THF (100 ml) at −78° C. under nitrogen was treated with butyllithium (1.6 M solution in hexane, 28 ml, 44.8 mmol). after being stirred for 1 hour at −78° C, the reaction mixture was warmed to room temperature and stirred for another hour. The reaction was quenched with water and the product was extracted with hexanes. The extract was dried over MgSO4, filtrated and concentrated in vacuo to give the product. (Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769)

後処理

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred for another hour
  3. customThe reaction was quenched with water
  4. extractionthe product was extracted with hexanes
  5. dry with materialThe extract was dried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. customto give the product

出典と根拠

ORDレコード
ord-f96ddd35dd0c48529e1aea558c55913b
出典データセット
uspto-grants-2002_03
特許番号
US06352990B1

反応ノート

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