반응 #46204

반응 방정식

H2O

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

BBr3

→

(3,4-dihydroxy-phenyl)-acetonitrile

수율 54.1%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   기타the CH2Cl2 layer was separated
4. 4
   추출The aqueous phase was extracted with CH2Cl2 (2×7 mL)
5. 5
   세척The combined organics were washed with brine
6. 6
   건조dried over Na2SO4
7. 7
   기타purified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

실험 절차

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).

출처