A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl est...

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Bibliographic Details
Published inJournal of chemical research Vol. 44; no. 5-6; pp. 301 - 304
Main Authors Wu, Xiaofang, Zhou, Lei, Yang, Ruoqi, Guo, Fengzhe, Tang, Zi-Long, Xiao, Jing
Format Journal Article
LanguageEnglish
Published London, England SAGE Publications 01.05.2020
Sage
Sage Publications Ltd
Subjects
Aliphatic compounds
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Chlorides
Esters
Physical Sciences
Science & Technology
Substrates
acid chlorides
phosphorus trichloride
chlorination
tert-butyl esters
chlorinating reagent
CONVERSION
OXALYL CHLORIDE
SEQUENCED REACTIONS
ANHYDRIDES
PEPTIDE
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ISSN1747-5198
2047-6507
DOI10.1177/1747519819898142

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Summary:For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.
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content type line 14
ISSN:1747-5198
2047-6507
DOI:10.1177/1747519819898142