Ethanol → Benzo(c)(1,2,5)oxadiazole-5-carbaldehyde

HRID 2085379Notes

Reaction equation

HRID 2085379 reaction equation
BrC([C:4]1[C:9]2=[N:10][O:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1)Br.C[CH2:14][OH:15]>O.[N+]([O-])([O-])=O.[Ag+]>[CH:14]([C:6]1[CH:5]=[CH:4][C:9]2[C:8]([CH:7]=1)=[N:12][O:11][N:10]=2)=[O:15]

Participants

5

Reactant 2

HCID 702EthanolHCID 22725207HCID 22725207, compound

Product 1

HCID 2776296Benzo(c)(1,2,5)oxadiazole-5-carbaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

AgNO3 (163 g) in 2 L of water was added to a refluxing mixture of dibromomethylbenzofurazan (122 g, 418 mmol) in EtOH (1 L). Heating at reflux temperature was continued for 2 h. The mixture was cooled, the precipitated AgBr was removed by filtration through Celite, and the solvent was concentrated. The resulting solution was extracted with toluene (10×100 mL), dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was chromatograghed (EtOAc/hexane, 1/125), giving the title aldehyde (48.2 g, 78%) as a white solid: 1H NMR δ 7.92 (m, 2H), 8.39 (s, 1 H), 10.10 (s, 1 H).

Workup

  1. temperatureHeating
  2. temperatureat reflux temperature
  3. temperatureThe mixture was cooled
  4. customthe precipitated AgBr was removed by filtration through Celite
  5. concentrationthe solvent was concentrated
  6. extractionThe resulting solution was extracted with toluene (10×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-20ee88b23ebd4e46ba0c50d6b180997b
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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