Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution
- Authors
- Song, Jiho; Kang, Hae Ju; Lee, Jung Wuk; Wenas, Michelle A.; Jeong, Seung Hwarn; Lee, Taeho; Oh, Kyungsoo; Min, Kyung Hoon
- Issue Date
- Aug-2017
- Publisher
- PUBLIC LIBRARY SCIENCE
- Citation
- PLOS ONE, v.12, no.8
- Journal Title
- PLOS ONE
- Volume
- 12
- Number
- 8
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/4068
- DOI
- 10.1371/journal.pone.0183575
- ISSN
- 1932-6203
- 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 degrees 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.
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