Triethyl phosphite → HCID 90403897, compound

Participants

Reaction Steps

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.

Provenance & Evidence