Reacción #1280058

Ecuación de reacción

water

Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate

sodium chloride

water

→

4-(2-Fluoro-4-nitrophenyl)butanenitrile

Rendimiento 65.0%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracting with ethyl acetate (2×50 mL)
2. 2
   SecadoThe organic layer was dried over MgSO4
3. 3
   Concentraciónconcentrated
4. 4
   Otrothe residue was purified with silica gel column chromatography (hexane:ethyl acetate, 8:1)

Procedimiento

A solution of compound Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate (73) (0.19 g, 0.59 mmol), sodium chloride (0.10 g, 1.76 mmol) and water (0.15 mL) in distilled dimethylsulfoxide (DMSO, 4 mL) was heated to 155° C. overnight. The reaction mixture was allowed to cool to 21° C. and then worked up by adding water and extracting with ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate, 8:1) to give desired 4-(2-Fluoro-4-nitrophenyl)butanenitrile (72) (79 mg, 65%): 1H NMR δ 8.02 (dd, 1H, J=8.3, 2.2 Hz), 7.94 (dd, 1H, J=9.5, 2.2 Hz), 7.42 (dd, 1H, J=8.3, 7.4 Hz), 2.93 (t, 2H, J=7.7 Hz) 2.41 (t, 2H, J=7.0 Hz) 2.01-2.07 (m, 2H).

Fuente