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

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...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 5; pp. 608 - 616
Main Authors Warashina, Takuya, Matsuura, Daisuke, Kimura, Yoshikazu
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.02.2019
Subjects
Alkyl formate
Fluorobenzene
N,N-dimethylformamide
N-methylformanilide
Oxalyl chloride
Piperonal
N-methylformanilide
N,N-dimethylformamide
Fluorobenzene
Piperonal
Alkyl formate
Oxalyl chloride
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.12.030