反応 #46204

反応方程式

H2O

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

BBr3

→

(3,4-dihydroxy-phenyl)-acetonitrile

収率 54.1%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他to quench
2. 2
   その他the reaction
3. 3
   その他the CH2Cl2 layer was separated
4. 4
   抽出The aqueous phase was extracted with CH2Cl2 (2×7 mL)
5. 5
   洗浄The combined organics were washed with brine
6. 6
   乾燥dried over Na2SO4
7. 7
   その他purified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

実験手順

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).

出典