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Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: Scope and limitations

Author:
Warashina, Takuya, Matsuura, Daisuke, Kimura, Yoshikazu
Source:
Tetrahedron 2019 v.75 no.5 pp. 608-616
ISSN:
0040-4020
Subject:
aluminum chloride, aromatic compounds, chemical reactions, chemical structure, ferric chloride, formates, methyl ethers, organochlorine compounds
Abstract:
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.
Agid:
6264352