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

HRID 1187090Notes

Reaction equation

HRID 1187090 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1579130802e849669d04a603112b0243
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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