1. Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution.
- Author
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Song, Jiho, Kang, Hae Ju, Lee, Jung Wuk, Wenas, Michelle A., Jeong, Seung Hwarn, Lee, Taeho, Oh, Kyungsoo, and Min, Kyung Hoon
- Subjects
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ETHERIFICATION , *BENZENE derivatives , *NUCLEOPHILIC substitution reactions , *ALKOXY group , *AROMATIC compounds , *X-ray crystallography - Abstract
In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min at 110°C in 10% dimethoxyethane in toluene, afforded the desired product in 87% yield with exclusive ortho-selectivity. A variety of reaction conditions were screened to obtain the maximum yield. The aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene with t-butoxide should be carried out under controlled conditions in order to avoid the formation of byproducts, unlike that of dihalogenated activated benzenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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