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

HRID 488719노트

반응식

HRID 488719 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 126397532,4-Dichloro-1-ethynylbenzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-541d3223f0ef42698ffbeb0a582955fb
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974808B2

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