151929-97-4Relevant academic research and scientific papers
Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution
Song, Jiho,Kang, Hae Ju,Lee, Jung Wuk,Wenas, Michelle A.,Jeong, Seung Hwarn,Lee, Taeho,Oh, Kyungsoo,Min, Kyung Hoon
, (2017/09/02)
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-dimethoxy-nitrobenzene 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 110C 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 ben-zenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography.
Synthesis of aryl ethers from aromatic carboxylic acids
Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
supporting information, p. 2387 - 2390 (2013/09/23)
A silver/copper bimetallic catalyst system promotes the decarboxylative Chan-Evans-Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C-H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.
Decarboxylative etherification of aromatic carboxylic acids
Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
, p. 9938 - 9941 (2012/08/08)
Decarboxylative Chan-Evans-Lam-type couplings are presented as a new strategy for the regiospecific construction of diaryl and alkyl aryl ethers starting from easily available aromatic carboxylic acids. They allow converting various aromatic carboxylate salts into the corresponding aryl ethers by reaction with alkyl orthosilicates or aryl borates, under aerobic conditions in the presence of silver carbonate as the decarboxylation catalyst and copper acetate as the cross-coupling catalyst.
