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- Title
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
- 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.
- Subjects
ETHERIFICATION; BENZENE derivatives; NUCLEOPHILIC substitution reactions; ALKOXY group; AROMATIC compounds; X-ray crystallography
- Publication
PLoS ONE, 2017, Vol 12, Issue 8, p1
- ISSN
1932-6203
- Publication type
Article
- DOI
10.1371/journal.pone.0183575