Triethyl phosphite → 5-Bromo-2,1,3-benzoxadiazole

HRID 1258313Notes

Reaction equation

HRID 1258313 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2=[N+:6]([O-])[O:7][N:8]=[C:4]2[CH:3]=1.P(OCC)(OCC)OCC>C(O)C.CCCCCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 5545145-Bromobenzo[c][1,2,5]oxadiazole 1-oxide

Product 1

HCID 27762985-Bromo-2,1,3-benzoxadiazoleYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-bromobenzo[c][1,2,5]oxadiazole 1-oxide (6.0 g, 28.436 mmol) in ethanol (60 mL) was added triethyl phosphite (6.2 mL, 34.123 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 60° C. for 1 h., cooled to RT, diluted with hexane (100 mL) and stirred for 10 min. The precipitated solid was filtered off and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 5-bromobenzo[c][1,2,5]oxadiazole (4.0 g, 71%) as a light yellow solid.

Workup

  1. temperaturecooled to RT
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto obtain the crude product
  5. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-d942439a188848dc80db10e6d5837c7e
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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