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On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

Name: On the hydrolysis of diethyl 2-(perfluorophenyl)malonate
Keywords: 2-(perfluorophenyl)acetic acid, QD241-441, Letter, Science, fluorinated aromatic compounds, Q, Organic chemistry, hydrolysis of esters, 2-(perfluorophenyl)malonic acid, decarboxylation

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 28 Jul 2020Publisher:Beilstein InstitutJournal:Beilstein Journal of Organic Chemistry, volume 16, pages 1,863-1,868 (eissn: 1860-5397,

Authors: Ilya V. Taydakov; Ilya V. Taydakov; Mikhail A. Kiskin;

doi: 10.3762/bjoc.16.153

pmid: 32802203

pmc: PMC7404147

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

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Abstract

Diethyl 2-(perfluorophenyl)malonate was synthesized in 47% isolated yield by the reaction of sodium diethyl malonate and hexafluorobenzene. The resulting compound was considered as a starting material for synthesizing 2-(perfluorophenyl)malonic acid by hydrolysis. It was found that the desired 2-(perfluorophenyl)malonic acid could not be obtained from this ester by hydrolysis, neither under basic nor under acidic conditions. Nevertheless, hydrolysis of the ester with a mixture of HBr and AcOH gave 2-(perfluorophenyl)acetic acid in a good preparative yield of 63%. A significant advantage of this new approach to 2-(perfluorophenyl)acetic acid is that handling toxic substances such as cyanides and perfluorinated benzyl halides is avoided.

Related Organizations

Russian Academy of Sciences
Russian Academy of Sciences
Russian Federation
Plekhanov Russian University of Economics
Russian Federation
Russian Academy of Sciences
P.N. Lebedev Physical Institute of the Russian Academy of Sciences
Russian Federation

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Keywords

2-(perfluorophenyl)acetic acid, QD241-441, Letter, Science, fluorinated aromatic compounds, Q, Organic chemistry, hydrolysis of esters, 2-(perfluorophenyl)malonic acid, decarboxylation

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CCDC 1993963: Experimental Crystal Structure Determination
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