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Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: Scope and limitations
Tetrahedron ( IF 2.1 ) Pub Date : 2018-12-19 , DOI: 10.1016/j.tet.2018.12.030
Takuya Warashina , Daisuke Matsuura , Yoshikazu Kimura

Practical preparations of dichloromethyl alkyl ethers are described, based on the reaction of alkyl formates with oxalyl chloride in the presence of N-methylformanilide. The method involves a simple procedure that does not require the use of harmful reagents. Dichloromethyl propyl and dichloromethyl butyl ethers represent secure synthetic equivalents to dichloromethyl methyl ether. Formylations of both electron-deficient and electron-rich aromatics with these dichloromethyl alkyl ethers in the presence of AlCl3, FeCl3, or TiCl4 have been systematically investigated. A plausible mechanism of formylation is discussed.



中文翻译:

二氯甲基烷基醚的高效制备及其在芳族化合物甲酰化中的应用:范围和局限性

基于烷基甲酸酯与草酰氯在N-甲基甲酰苯胺存在下的反应,描述了二氯甲基烷基醚的实际制备。该方法涉及简单的程序,不需要使用有害试剂。二氯甲基丙基醚和二氯甲基丁基醚代表二氯甲基甲基醚的安全合成等价物。已经在AlCl 3,FeCl 3或TiCl 4的存在下系统地研究了缺电子和富电子芳族化合物与这些二氯甲基烷基醚的甲酰化反应。讨论了甲酰化的合理机制。

更新日期:2018-12-19
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