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关于2-(全氟苯基)丙二酸二乙酯的水解。

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate.

作者信息

Taydakov Ilya V, Kiskin Mikhail A

机构信息

P.N. Lebedev Physical Institute of the Russian Academy of Sciences. Leninskiy prospect, 53, Moscow, GSP-1, 119991, Russian Federation.

G.V. Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow, 117997, Russian Federation.

出版信息

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

DOI:10.3762/bjoc.16.153
PMID:32802203
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7404147/
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.

摘要

丙二酸二乙酯与六氟苯反应，以47%的分离产率合成了2-(全氟苯基)丙二酸二乙酯。所得化合物被视为通过水解合成2-(全氟苯基)丙二酸的起始原料。结果发现，无论是在碱性条件下还是酸性条件下，该酯水解均无法得到所需的2-(全氟苯基)丙二酸。然而，该酯用HBr和AcOH的混合物水解，以63%的良好制备产率得到了2-(全氟苯基)乙酸。这种制备2-(全氟苯基)乙酸的新方法的一个显著优点是避免了处理氰化物和全氟苄基卤等有毒物质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/02672712bbcc/Beilstein_J_Org_Chem-16-1863-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/d02eec465d55/Beilstein_J_Org_Chem-16-1863-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/80d2b864d47d/Beilstein_J_Org_Chem-16-1863-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/58b42f7e516a/Beilstein_J_Org_Chem-16-1863-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/75f3606a8809/Beilstein_J_Org_Chem-16-1863-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/c6293d193f13/Beilstein_J_Org_Chem-16-1863-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/8ce48cc6f900/Beilstein_J_Org_Chem-16-1863-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/02672712bbcc/Beilstein_J_Org_Chem-16-1863-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/d02eec465d55/Beilstein_J_Org_Chem-16-1863-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/80d2b864d47d/Beilstein_J_Org_Chem-16-1863-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/58b42f7e516a/Beilstein_J_Org_Chem-16-1863-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/75f3606a8809/Beilstein_J_Org_Chem-16-1863-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/c6293d193f13/Beilstein_J_Org_Chem-16-1863-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/8ce48cc6f900/Beilstein_J_Org_Chem-16-1863-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42e1/7404147/02672712bbcc/Beilstein_J_Org_Chem-16-1863-g008.jpg

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