Development of a Practical and Efficient Synthesis of Chloromethyl 2-Ethoxy-2-methylpropanoate

Autor:	Cawley James Joseph, Roberto Colon-Cruz, Nathan D. Ide, Brian C. Vanderplas, Rajesh Kumar, Zhihui Peng, Weiling Cai, John A. Ragan
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Sodium bisulfite Organic Chemistry Alkoxy group Alkyl bromide Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 14:1402-1406
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op1002038
Popis:	An efficient synthesis of chloromethyl 2-ethoxy-2-methylpropanoate from 2-bromoisobutyric acid is reported. Four developments were key to this route: (i) a mild, base-mediated ethanolysis of a tertiary alkyl bromide, (ii) a sodium bisulfite purge of 2-methylacrylic acid, (iii) preparation of a thiomethyl ester via a formal Pummerer process with DMSO, and (iv) improved conversion of a thiomethyl ester to a chloromethyl ester through suppression of a competing chlorination pathway.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9b8b464ce0b79e60b40fb2ac85f441e8 https://doi.org/10.1021/op1002038 Zobrazit plný text záznamu