반응 #67426

반응 방정식

6-chloromethyl-4-fluoro-benzo[1,3]dioxole

NaCN

water

→

2-(7-fluorobenzo[d][1,3]dioxol-5-yl)acetonitrile

수율 70.0%

용매

DMSO

반응 조건

후처리

1. 1
   추출The mixture was extracted with EtOAc (50 mL×3)
2. 2
   세척The combined organic layers were washed with water (50 mL) and brine (50 mL)
3. 3
   건조dried over Na2SO4
4. 4
   기타evaporated under reduced pressure
5. 5
   기타to give the crude product, which
6. 6
   기타was purified by column chromatography on silica gel (petroleum ether/E.A.=10/1)

실험 절차

A mixture of 6-chloromethyl-4-fluoro-benzo[1,3]dioxole (0.80 g, 4.3 mmol) and NaCN (417 mg, 8.51 mmol) in DMSO (20 mL) was stirred at 30° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/E.A.=10/1) to afford 2-(7-fluorobenzo[d][1,3]dioxol-5-yl)acetonitrile (530 mg, 70%). 1H NMR (300 MHz, CDCl3) 6.68-6.64 (m, 2H), 6.05 (s, 2H), 3.65 (s, 2H). 13C-NMR δ151.1, 146.2, 134.1, 124.2, 117.5, 110.4, 104.8, 102.8, 23.3.

출처