Hydrochloric Acid → 1-(3-Bromo-1,2-oxazol-5-yl)ethan-1-one

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Reaction Steps

A mixture of dibromoformaldoxime(which was obtained in Example 116) (32.5 g, 160.2 mmol), 3-butyn-one (13.41 g, 197 mmol), potassium carbonate (11 g, 80.1 mmol), and methylene chloride (300 mL) was stirred at ambient temperature for 20 hours. The slurry was then treated with aqueous hydrochloric acid (2 N, 200 mL) and extracted with methylene chloride. The combined organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (ethyl acetate/hexanes 5/95) gave a white solid (16.76 g, 56% yield); 1H NMR (300 MHz, CDCl3) δ 2.62 (s, 3H), 6.97 (s, 1H).

Provenance & Evidence