Reacción #1350610

Ecuación de reacción

NBS

benzoylperoxide

2-fluoro-4-cyanotoluene

compound 38

2-fluoro-4-cyanotoluene

→

3-fluoro-4-(bromomethyl)benzonitrile

Rendimiento 31.1%

Disolventes

ether

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling down to ambient temperature
2. 2
   Lavadowashed with aqueous Na2S3O3
3. 3
   Secadodried (MgSO4)
4. 4
   OtroRemoval of solvent under vacuum
5. 5
   Otrowas purified by flash chromatography

Procedimiento

NBS (Aldrich, 3.02 g, 17 mmol) and benzoylperoxide (Aldrich, 0.37 g, 1.5 mmol) was added to a solution of 2-fluoro-4-cyanotoluene (compound 38, 2.08 g, 15 mmol) in CCl4. The reaction mixture was heated at 80° C. for 14 hours. After cooling down to ambient temperature, the mixture was diluted with ether (100 mL) and washed with aqueous Na2S3O3, and dried (MgSO4). Removal of solvent under vacuum led to a yellow oil which was purified by flash chromatography. The title compound 39 (1.4 g, 42%) was obtained, together with a by-product, 3-fluoro-4-(bromomethyl)benzonitrile (40) (1.0 g, 30 %). For the title compound (39): 1HNMR (CDCl3) δ4.46 (s, 2H), 7.35 (d, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.52 (t, 1H, J=8.0 Hz). For the by-product (40): 1HNMR (CDCl3) δ6.90 (s, 1H), 7.35 (d, 1H, J=8.0 Hz), 7.55 (d, 1H, J=8.0 Hz), 7.96 (t, 1H, J=8.0 Hz).

Fuente