Reaction of Organic Halogen Compounds with Potassium Fluoride. (Ⅲ) Fluorination of Aromatic vic-dihalides

有機할로겐化合物과 KF의 反應 (第3報) 芳香族이웃디할라이드의 弗化反應

  • You Sun Kim (Chemistry Division, Atomic Energy Research Institute) ;
  • Ki Soo Kim (Chemistry Division, Atomic Energy Research Institute)
  • 김유선 (原子力硏究所 化學硏究室) ;
  • 김기수 (原子力硏究所 化學硏究室)
  • Published : 19690300

Abstract

Flourination of Ethyl, ${\alpha},{\beta$}-dichloro-${\beta$}-phenyl propionate, Ethyl ${\alpha},{\beta$}-dibromo ${\beta$}-phenyl propionate, Ethyl ${\alpha},{\beta$}-dichloro ${\beta$}-(p-chloro-phenyl) propionate, and dibromostyrene by potassium fluoride were investigated in presence of dimethyl formamide, diethylene glycol, and diethylene glycol monomethyl-ether. The reactivity of these organic halogen esters and hydrocarbons towards potassium fluoride was checked further by means of radioactive fluorine-18. tracer. Generally, the reaction gave monofluoride together with dehalogenated olefin. The formation of olefine was increased when the reaction was done at high reaction temperature in presence of diethylene glycol, whereas the lower reaction temperature in presence of diethyleneglycol monomethyl ether favored the formation of mono fluoride in a good yield. The procedures and methods of the identification of monofluorides were described and the feasibility of this reaction of fluorine containing ester including the F-18 labelled compounds was discussed.

${\alpha},{\beta$}-dichloro-${\beta$}-phenyl propionate, Ethyl ${\alpha},{\beta$}-dibromo-${\beta$}-phenyl propionate, Etyyl ${\alpha},{\beta$}-dichloro-${\beta$}-(p-chlorophenyl)propionate, 및 dibromo-styrene 等의 化合物을 各種溶媒(dimethly formamide, diethylene glycol, 및 diethylene glyco monomethyl ether 等) 存在下에서 弗化反應을 시켜 보았으며 放射性弗素-18을 追跡子로 使用하여서 위의 化合物들의 弗化카리에 對한 反應度를 檢査하여 보았다. 一般的으로 弗化反應 生成物은 모노弗化物과 脫할로겐된 二重結合物을 生成하였다. diethylglycol 存在下에서 高溫反應시킨 條件下에서는 二重結合生成物이 많았고 diethylene glyco-monoethyl ether 存在下에서 低溫反應시킨 條件下에서는 弗化物이 多量生成하였다. 모노弗化物의 合成方式 및 確認方法에 關하여 說明하였으며 本反應의 合成上의 用途($F^{18}$ 標識化合物包含)에 言及하였다.

Keywords

References

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