Reaktion #8308

Reaktionsgleichung

1-chloromethyl-4-fluoronaphthalene

sodium cyanide

water

→

title compound

(4-Fluoronaphthalen-1-yl)acetonitrile

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to room temperature
2. 2
   Sonstigepartitioned between saturated sodium bicarbonate solution and ethyl acetate
3. 3
   WaschenThe organic portion is washed with three portions of water, one portion of brine
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

Vorschrift

A solution of 1-chloromethyl-4-fluoronaphthalene (5.45 g, 5.66 mmol), sodium cyanide (333 mg, 6.79 mmol), and water (2 mL) in N,N-dimethylformamide (30 mL) is stirred for 8 h, then heated at 70° C. for 15 h. The mixture is cooled to room temperature and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic portion is washed with three portions of water, one portion of brine, dried (sodium sulfate), filtered and evaporated. The residue is chromatographed on SiO2 (30% ethyl acetate/hexane) to yield the title compound, 4.67 g (90%), as a light brown solid. 1H NMR (CDCl3): δ 8.19 (d, J=8 Hz, 1H), 7.87 (d, J=8 Hz, 1H), 7.68 (ddd, J=8, 7, 1 Hz, 1H), 7.63 (ddd, J=8, 7, 1 Hz, 1H), 7.51 (dd, J=8, 5 Hz, 1H), 7.14 (dd, J=10, 8 Hz, 1H), 4.09 (s, 2H).

Quelle