Triethyl phosphite → HCID 90404070, compound

HRID 1468964Notes

Reaction equation

HRID 1468964 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2=[N+:6]([O-])[O:7][N:8]=[C:4]2[C:3]=1[Cl:12].P(OCC)(OCC)OCC>C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][O:7][N:8]=[C:4]2[C:3]=1[Cl:12]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 90403883HCID 90403883, compound

Product 1

HCID 90404070HCID 90404070, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 5-bromo-4-chlorobenzo[c][1,2,5]oxadiazole 1-oxide (3.2 g, 12.8 mmol) was stirred in 50 ml ethanol, treated with triethyl phosphite (3.2 g, 19 mmol) and heated to reflux for 5 h. After cooling, the volatiles were removed by rotary evaporation, the residue was taken up in 75 mL dichloromethane and stirred with 20 mL bleach solution for 20 min. The organic phase was washed with 10 mL saturated NaCl, dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography on silica to give the title compound as an orange solid (1.5 g, 50%): mp 96-97° C.; 1H NMR (400 MHz, CDCl3) δ 7.68 (d, J=9.4 Hz, 1H), 7.59 (d, J=9.3 Hz, 1H); EIMS m/z 232.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. customthe volatiles were removed by rotary evaporation
  5. washThe organic phase was washed with 10 mL saturated NaCl
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe crude material was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-24a32f47df9e4b52bd63b9d03b04866a
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

Loading…