تفاعل #8308

معادلة التفاعل

1-chloromethyl-4-fluoronaphthalene

sodium cyanide

water

→

title compound

(4-Fluoronaphthalen-1-yl)acetonitrile

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to room temperature
2. 2
   أخرىpartitioned between saturated sodium bicarbonate solution and ethyl acetate
3. 3
   غسيلThe organic portion is washed with three portions of water, one portion of brine
4. 4
   تجفيفdried (sodium sulfate)
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

الإجراء التجريبي

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).

المصدر