Reacción #8308

Ecuación de reacción

1-chloromethyl-4-fluoronaphthalene

sodium cyanide

water

→

title compound

(4-Fluoronaphthalen-1-yl)acetonitrile

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled to room temperature
2. 2
   Otropartitioned between saturated sodium bicarbonate solution and ethyl acetate
3. 3
   LavadoThe organic portion is washed with three portions of water, one portion of brine
4. 4
   Secadodried (sodium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

Procedimiento

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).

Fuente