Triethyl phosphite → HCID 90403897, compound

HRID 1468971Notes

Reaction equation

HRID 1468971 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([C:11]=1[CH3:12])=[N+:7]([O-])[O:8][N:9]=2.P(OCC)(OCC)OCC>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[N:9][O:8][N:7]=[C:6]2[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 90404007HCID 90404007, compound

Product 1

HCID 90403897HCID 90403897, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 6-bromo-7-methylbenzo[c][1,2,5]oxadiazole 1-oxide (7.0 g, 31 mmol) from the above step was slurried in 100 ml ethanol, treated with triethyl phosphite (6.2 g, 37 mmol) and heated to reflux for 20 h. The volatiles were removed by rotary evaporation, the residue taken up in 100 mL dichloromethane and stirred with 50 mL 5% bleach solution for 20 min. The organic phase was washed with 20 mL saturated NaCl, dried (Na2SO4) and evaporated. The material was purified by flash chromatography with 0-30% ethyl acetate-hexane gradient to give the title compound as an orange solid (3.6 g, 55%): mp 80-83° C.; 1H NMR (400 MHz, Chloroform-d) δ 7.56 (d, J=9.3, 1H), 7.50 (d, J=9.4 Hz, 1H), 2.71 (s, 3H). EIMS m/z 212.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 h
  3. customThe volatiles were removed by rotary evaporation
  4. washThe organic phase was washed with 20 mL saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe material was purified by flash chromatography with 0-30% ethyl acetate-hexane gradient

Sources & evidence

ORD record
ord-485dfe735450404f9838cc92102a2334
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

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