반응 #46184

반응 방정식

4-bromomethyl-1-chloro-2-methoxy-benzene

NaCN

→

2-(4-chloro-3-methoxyphenyl)acetonitrile

수율 48.0%

용매

C2H5OH

반응 조건

후처리

1. 1
   기타Ethanol was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in H2O
3. 3
   추출The mixture was extracted with ethyl acetate (300 mL×3)
4. 4
   세척The combined organic layers were washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   기타purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1)

실험 절차

To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.29 mol) in C2H5OH (90%, 500 mL) was added NaCN (28.5 g, 0.58 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.

출처