Reacción #158528

Ecuación de reacción

Diethyl 2-bromo-2-methylmalonate

potassium fluoride

3-nitrophenol

→

diethyl 2-methyl-2-(3-nitrophenoxy)malonate

Rendimiento 80.0%

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Extracciónextracted with ethyl acetate (3×200 mL)
3. 3
   LavadoThe organic layer was washed with aq. 1N NaOH (2×75 mL)
4. 4
   Secadodried over anhydrous Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated in vacuo

Procedimiento

Diethyl 2-bromo-2-methylmalonate (1.0 g, 3.95 mmole) was added to a stirred suspension of potassium fluoride (0.57 g, 9.8 mmole) in dry DMF (5 mL). After stifling for 20 min at room temperature, 3-nitrophenol (0.55 g, 3.95 mmole) was added. The resulting mixture was stirred at 60° C. for 6 h, cooled to room temperature, diluted with water (30 mL) and extracted with ethyl acetate (3×200 mL). The organic layer was washed with aq. 1N NaOH (2×75 mL), dried over anhydrous Na2SO4, filtered and evaporated in vacuo to provide diethyl 2-methyl-2-(3-nitrophenoxy)malonate (0.89 g, 80%). 1H NMR (CDCl3): δ 7.92 (dd, 1H, J=2.3 and 8.2 Hz), 7.82 (t, 1H, J=2.3 Hz), 7.41 (t, 1H, J=8.2 Hz), 7.30 (dd, 1H, J=2.3 and 8.2 Hz), 4.28 (qt, 4H, J=7.0 Hz), 1.81 (s, 3H), 1.26 (t, 6H, J=7.0 Hz).

Fuente