반응 #8308

반응 방정식

1-chloromethyl-4-fluoronaphthalene

sodium cyanide

water

→

title compound

(4-Fluoronaphthalen-1-yl)acetonitrile

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도The mixture is cooled to room temperature
2. 2
   기타partitioned between saturated sodium bicarbonate solution and ethyl acetate
3. 3
   세척The organic portion is washed with three portions of water, one portion of brine
4. 4
   건조dried (sodium sulfate)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

실험 절차

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).

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