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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 18, Number 4
JKCSEZ 18(4)
August 20, 1974 

A Convenient Preparation of Polychloroanisidine and Fluorochloroanisole Derivatives

Polychloroanisidine 및 Fluorochloroanisole 유도체의 간편한 합성
You Sun Kim, Tae Young Kim, Yun Hee Kim

김유선, 김태영, 김윤희
P-dichlorobenzene을 출발물질로하여 니트로화 반응, 메톡시화 반응 및 환원반응을 거쳐서 2-amino-4-chloroanisole을 얻은 다음 이것에 연속적인 염소화반응을 시켜 2-amino-3,4,5-trichloroanisole 만을 순수하게 얻을 수 있었다. 한편 4-chloro-2-nitroanisole 을 촉매 존재하에서 염소화반응시켜 2,4-dichloro-6-nitroanisole을 간편하게 합성할 수 있었다. 염소화반응생성물들의 확인에 NMR 분석방식을 사용하여 생성물을 분리하지 않고 연속 합성하는 방식을 택하였으며 이러한 방식의 간편성을 논의 하였다. 높은 합성수득률 및 반응조건의 간이성에 따르는 실용성에 관하여서도 각각 제언 하였다.

Starting from p-dichlorobenzene, 2-amino-4-chloroanisole could be prepared via a nitration, a methoxylation, and subsequent reduction. The repeated chlorination of 2-amino-4-chloroanisole resulted 2-amino-3,4,5-trichloroanisole without any isomeric products. The chlorination of 4-chloro-2-nitroanisole could easily give 2,4-dichloro-6-nitroanisole but polychlorination of the product could not be achieved at the atmospherical pressure. The repeated chlorination of 2-amino-4,6-dichloroanisole could give 2-amino-3,4,5,6-tetrachloroanisole, The Schiemann reaction of 2-amino-4-chloroanisole and 2-amino-4,6-dichloroanisole could give 2-fluoro-4-chloroanisole and 2-fluoro-4,6-dichloroanisole, respectively. The repeated chlorination of these fluorochloroanisoles could give 2-fluoro-3,4,5,6-tetrachloroanisole. In each chlorination process, the components of products were examined by means of NMR spectrometry and the chlorination reaction was repeated without isolating each isomeric product. The feasibility of the present routes of preparations was discussed in respects to the conveniency of reaction conditions and respective overall yields of the processes.

278 - 288
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