Reaktion #67426

Reaktionsgleichung

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

NaCN

water

→

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

Ausbeute 70.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle