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

HRID 655432Notes

Reaction equation

HRID 655432 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-ea1fab5159ee4aaa95f1f9122f8a2aa4
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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