Reaktion #590407

Reaktionsgleichung

H2O

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

BBr3

→

(3,4-dihydroxy-phenyl)-acetonitrile

Ausbeute 54.1%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   Sonstigethe CH2Cl2 layer was separated
4. 4
   ExtraktionThe aqueous phase was extracted with CH2Cl2 (2×7 mL)
5. 5
   WaschenThe combined organics were washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigepurified by column chromatography on silica gel (petroleum ether/ethyl acetate 5:1)

Vorschrift

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/ethyl acetate 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).

Quelle