Ethanol → 5-Ethenyl-2,1,3-benzoxadiazole

HRID 1187090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187090
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.[CH2:11](O)[CH3:12]>>[CH:11]([C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1)=[CH2:12]

Komponenten

3

Edukt 2

HCID 702EthanolHCID 27762985-Bromo-2,1,3-benzoxadiazole

Produkt 1

HCID 595687205-Ethenyl-2,1,3-benzoxadiazole

Versuchsvorschrift

5-Bromo-2,1,3-benzoxadiazole (5.5 g, 27.6 mmol)), potassium vinylfluoroborate (7.40 g, 55.3 mmol), and PdCl2(dppf)-CH2Cl2Adduct (1.088 g, 1.332 mmol) were suspended in ethanol (75 ml) then added TEA (7.70 ml, 55.3 mmol). The reaction mixture was then degassed and heated to reflux for 3 hrs. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified through a 330 g ISCO Redi-Sep silica gel plug and eluted with 20% ETOAc/hexane to yield 5-ethenyl-2,1,3-benzoxadiazole.

Aufarbeitung

  1. customThe reaction mixture was then degassed
  2. temperatureheated
  3. temperatureto reflux for 3 hrs
  4. additionThe reaction was diluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified through a 330 g ISCO Redi-Sep silica gel plug
  10. washeluted with 20% ETOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-1579130802e849669d04a603112b0243
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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