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A new, mild, and efficient synthesis of 2,2-difluoro-3-hydroxyacids through a selective haloform reaction

AuthorsJiménez, Óscar; Bosch, María Pilar ; Guerrero, Ángel
KeywordsFluoroorganic chemistry
Selective Haloform Reaction
Fluorine source
Issue Date16-Nov-2005
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 70(26): 10883–10885 (2005)
AbstractLong-chain 2,2-difluoro-3-hydroxyacids have been synthesized in a new, straightforward manner by treatment of 4-hydroxy-1,1,1,3,3-pentafluoroalkyl ketones, easily obtained by reaction of pentafluoroenolate 2 with aldehydes and ketones, with base under mild conditions. The reaction sequence is marked by the selective cleavage of the CO−CF3 bond, as well as the absence of products arising from the alternative CO−CF2R bond cleavage. The process represents a convenient approach for the synthesis of 2,2-difluoro-3-hydroxyacids, as it is short, provides good to excellent yields under mild conditions, and uses hexafluoro-2-propanol, a very cheap reagent, as the fluorine source.
Description3 pages, 2 schemes, 1 chart, 1 table.-- PMID: 16356015 [PubMed].-- Printed version published Dec 23, 2005.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0518856
Publisher version (URL)http://dx.doi.org/10.1021/jo0518856
Appears in Collections:(IQAC) Artículos
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