Preparation method of dicyanonorbornane
A technology of norbornane and dicyano, which is applied in the field of preparation of dicyanonorbornane, can solve the problems of complicated operation, easy occurrence of danger, low yield and the like, and achieves simple preparation process, high purity and high yield Effect
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[0026] The invention provides a kind of preparation method of dicyano norbornane, comprising:
[0027] The compound of formula (Y) structure is reacted with a cyanide reagent under catalyst conditions to obtain dicyano-norbornane;
[0028] Wherein, the catalyst is tetrabutylammonium iodide, tetrabutylammonium fluoride, tetrabutylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium hydroxide, 15-Crown-5 and sodium iodide one or several.
[0029]
[0030] where the R 3 , R 4 are independently selected from halogen or cyano.
[0031] According to the present invention, the present invention reacts the compound of the formula (Y) structure with a cyanide reagent under catalyst conditions to obtain dicyano norbornane; in the compound of the formula (Y), the R3, R 4 independently selected from chlorine, bromine, iodine or cyano, more preferably independently selected from chlorine, bromine or cyano; the cyanide reagent is preferably sodium cyanide, zinc cyanide, ...
Embodiment 1
[0039] Weigh 1.1916g cyano norbornene (bicyclo[2.2.1]-5-heptene-2-carbonitrile) in a 50ml single-necked flask, add 3.0g40% hydrochloric acid therein, then at T=80°C React in an oil bath for 10 hours. After the reaction is completed, extract the system with ethyl hexanoate to obtain 1.91g of cyanonorbornane containing -Br. After repeating the above steps, a total of 3.81g of cyanonorbornane containing -Br is obtained. ; Its yield is shown in Table 1.
[0040] Weigh 2.00 g of cyano-norbornane containing -Br obtained in the above steps in a 50 ml single-necked flask, add 1.48 g of tetrabutylammonium iodide, 1.22 g of sodium cyanide, and 24.0 g of dimethyl sulfoxide , and then reacted in an oil bath at T=130° C. for 8 hours, then filtered the system, and removed the solvent by rotary evaporation to obtain 1.36 g of dicyanonorbornane. The yield and purity are shown in Table 1.
[0041] The structure of the obtained dicyano norbornane is identified, the results are shown in figure...
Embodiment 2
[0043] Weigh 92.14g norbornadiene (2,5-norbornadiene) in a 500ml one-necked flask, add 276.42g35% hydrochloric acid therein, then react in an oil bath of T=90°C for 9h, and use The system was extracted with ethyl hexanoate to obtain 153.51 g of norbornane containing -C1; the yield is shown in Table 1.
[0044]After repeating the above steps, a total of 307.01g of norbornane containing-Cl was obtained; 165.06g of norbornane containing-Cl obtained in the above steps was weighed in a 5000ml single-necked flask, and 52.29g of tetrabutylammonium fluoride was added thereto 140.92g of zinc cyanide was added, 1650g of toluene was added, and then the reaction was carried out in an oil bath at T=140°C for 8h. After that, the system was filtered, and the solvent was removed by rotary evaporation to obtain 135.96g of dicyanonorbornane. Its yield and purity are shown in Table 1.
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