On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

Ilya V Taydakov; Mikhail A Kiskin

doi:10.3762/bjoc.16.153

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

Beilstein J Org Chem. 2020 Jul 28:16:1863-1868. doi: 10.3762/bjoc.16.153. eCollection 2020.

Authors

Ilya V Taydakov^{1

2}, Mikhail A Kiskin³

Affiliations

¹ P.N. Lebedev Physical Institute of the Russian Academy of Sciences. Leninskiy prospect, 53, Moscow, GSP-1, 119991, Russian Federation.
² G.V. Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow, 117997, Russian Federation.
³ N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy prospect, 31, Moscow, GSP-1, 119991, Russian Federation.

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.

Keywords: 2-(perfluorophenyl)acetic acid; 2-(perfluorophenyl)malonic acid; decarboxylation; fluorinated aromatic compounds; hydrolysis of esters.

Grants and funding

This work was financially supported by the Russian Science Foundation (Project №19-13-00272).