Reacción #46204

Ecuación de reacción

H2O

benzo[1,3]dioxol-5-yl-acetonitrile

BBr3

→

(3,4-dihydroxy-phenyl)-acetonitrile

Rendimiento 54.1%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench
2. 2
   Otrothe reaction
3. 3
   Otrothe CH2Cl2 layer was separated
4. 4
   ExtracciónThe aqueous phase was extracted with CH2Cl2 (2×7 mL)
5. 5
   LavadoThe combined organics were washed with brine
6. 6
   Secadodried over Na2SO4
7. 7
   Otropurified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

Procedimiento

To a solution of benzo[1,3]dioxol-5-yl-acetonitrile (0.50 g, 3.1 mmol) in CH2Cl2 (15 mL) was added dropwise BBr3 (0.78 g, 3.1 mmol) at −78° C. under N2. The mixture was slowly warmed to room temperature and stirred overnight. H2O (10 mL) was added to quench the reaction and the CH2Cl2 layer was separated. The aqueous phase was extracted with CH2Cl2 (2×7 mL). The combined organics were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1) to give (3,4-dihydroxy-phenyl)-acetonitrile (0.25 g, 54%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.07 (s, 1H), 8.95 (s, 1H), 6.68-6.70 (m, 2H), 6.55 (dd, J=8.0, 2.0 Hz, 1H), 3.32 (s, 2H).

Fuente