Novel Synthesis of Desymmetrized Resorcinol Derivatives: Aryl Fluoride Displacement on Deactivated Substrates
摘要:
A short, high-yielding synthesis of differentially substituted resorcinol derivatives has been developed that utilizes 1,3difluorobenzene as the starting material and employs sequential nucleophilic aromatic substitution (SNAr) reactions to generate desymmetrized products. The scope and limitations of the second SNAr reaction on the deactivated 1-alkoxy-3-fluorobenzene intermediates have been investigated. This methodology has also been employed in the synthesis of desymmetrized catechol derivatives from 1,2difluorobenzene.
Ethers made easy: Heating a solution containing a tosylhydrazone and either a phenol or an alcohol in the presence of K2CO3 leads to the corresponding ethers (see scheme; MW=microwave, Ts=tosyl). The reaction is fairly general for the preparation of aryl alkyl and alkyl alkyl ethers, and represents a new method for the reductive etherification of carbonylcompounds.
醚变得容易:在K 2 CO 3存在下加热含有甲苯磺酰s和苯酚或醇的溶液会生成相应的醚(参见方案; MW =微波,Ts =甲苯磺酰基)。该反应对于制备芳基烷基和烷基烷基醚是相当普遍的,并且代表了一种用于羰基化合物的还原醚化的新方法。