Potassium Hydroxide → 5-(2,4-dichlorophenoxy)benzo-2,1,3-oxadiazole N-oxide

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Reaction Steps

2-Nitro-5-(2,4-dichlorophenoxy)aniline (1.6 g, 5.4 mmol) is dissolved in a solution of potassium hydroxide (0.33 g, 5.9 mmol) in ~150 ml of ethanol. The mixture is cooled to -5°, and sodium hypochlorite (17 ml of 5.3% solution, 0.9 g, 11.8 mmol) is added dropwise over 20 minutes. The reaction is stirred at RT overnight, then cooled to 10° and ~2 ml of sodium hypochlorite is added. One hour later, the reaction is stripped. The residue is taken up in ether, washed with water, dried, stripped and purified by prep. TLC (10% ethyl acetate/hexane) to yield 5-(2,4-dichlorophenoxy)benzo-2,1,3-oxadiazole N-oxide, m.p. 92°-93°.

Provenance & Evidence