Reacción #582509

Ecuación de reacción

[ 2 ]

4′-Bromo-2-(4-bromobenzoyl)acetophenone

hydroxylamine hydrogen chloride

NaOH

→

3,5-Bis(4-bromophenyl)isoxazole

Disolventes

dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux
3. 3
   Otrothe solvent was removed in vacuo
4. 4
   OtroThe product was recrystallized from ethanol

Procedimiento

In a 250 ml round bottom flask, 4 g (10.4 mmol) of [2] was dissolved in 100 ml dry dioxane and heated to reflux, then 3.0 g (43.2 mmol) hydroxylamine hydrogen chloride in 10 ml water and 5 ml (25 mmol) 5 N NaOH was then dropped into the refluxing mixture. After 12 hours, the reaction mixture was cooled down to room temperature, and the solvent was removed in vacuo. The product was recrystallized from ethanol. Characterization. Yield: 3.41 g (85%). M.P. 218.5-219.5° C. 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.78 (d, 2H, ArH), 7.74 (d, 2H, Ar′H), 7.66 (d, 2H, ArH), 7.6 (d, 2H, Ar′H), 6.82 (s, 1H, isoxazole proton). EI-MS: 379(M+), 224, 183, 155.

Fuente