Reacción #7798

Ecuación de reacción

4-bromo-2-fluoro benzyl bromide

sodium cyanide

→

4-bromo-2-fluoro benzyl cyanide

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled at rt
2. 2
   Otroquenched with brine (50 mL)
3. 3
   ExtracciónAfter extraction with EtOAc (3×50 mL)
4. 4
   Lavadowashed with brine (50 mL)
5. 5
   Secadodried (MgSO4)
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe residue was purified by chromatography on silica gel using
8. 8
   workup.ADDITIONa mixture of hexanes:EtOAc (5:1)

Procedimiento

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The resulting mixture was stirred at 90° C. for 1 h, cooled at rt and quenched with brine (50 mL). After extraction with EtOAc (3×50 mL), the organic layers were combined, washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexanes:EtOAc (5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

Fuente