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Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution.


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.

SUBMITTER: Song J 

PROVIDER: S-EPMC5568332 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution.

Song Jiho J   Kang Hae Ju HJ   Lee Jung Wuk JW   Wenas Michelle A MA   Jeong Seung Hwarn SH   Lee Taeho T   Oh Kyungsoo K   Min Kyung Hoon KH  

PloS one 20170823 8


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 exclusiv  ...[more]

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