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

HRID 1474348Notes

Reaction equation

HRID 1474348 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-c1491ce5133c4945bbfd30ba659086c1
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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