反応 #8308

反応方程式

1-chloromethyl-4-fluoronaphthalene

sodium cyanide

water

→

title compound

(4-Fluoronaphthalen-1-yl)acetonitrile

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度The mixture is cooled to room temperature
2. 2
   その他partitioned between saturated sodium bicarbonate solution and ethyl acetate
3. 3
   洗浄The organic portion is washed with three portions of water, one portion of brine
4. 4
   乾燥dried (sodium sulfate)
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他The residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

実験手順

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).

出典