Réaction #46204

Équation de réaction

H2O

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

BBr3

→

(3,4-dihydroxy-phenyl)-acetonitrile

Rendement 54.1%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autreto quench
2. 2
   Autrethe reaction
3. 3
   Autrethe CH2Cl2 layer was separated
4. 4
   ExtractionThe aqueous phase was extracted with CH2Cl2 (2×7 mL)
5. 5
   LavageThe combined organics were washed with brine
6. 6
   Séchagedried over Na2SO4
7. 7
   Autrepurified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

Mode opératoire

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).

Source