An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol

An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2021, Volume: 70, Number: 5, Pages: 995-998 Pages count : 4 DOI: 10.1007/s11172-021-3178-3

Tags

aromatic nucleophilic substitution reaction; fluorinated phenols; organofluorine compounds; polyfluorinated aromatic sulfides; reduction of sulfide

Authors

Tretyakov E.V. ¹ , Maksimov A.M. ² , Nikul’shin P.V. ² , Mezhenkova T.V. ²

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991, Russian Federation
2	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentreva, Novosibirsk, 630090, Russian Federation

A new method for the preparation of 2,3,4,5-tetrafluorophenol from 2-[(2,3,4,5,6-pentafluorophenyl)thio]acetic acid has been proposed. It included the intramolecular cyclization of the salt of this acid in the presence of K2CO3 with the substitution of the ortho fluorine atom and the formation of a lactone, which under the reaction conditions underwent the ring-opening with the formation of the potassium salt of 2-[6-hydroxy(2,3,4,5-tetrafluorophenyl)-thio]acetic acid. The resulting salt was converted into methyl ester and desulfurized with Raney nickel to 2,3,4,5-tetrafluorophenol. The proposed method is a simple and efficient way to obtain poorly available 2,3,4,5-tetrafluorophenol in ∼58% total yield based on 2-[(2,3,4,5,6-pentafluorophenyl)thio]acetic acid. © 2021, Springer Science+Business Media LLC.

Tretyakov E.V. , Maksimov A.M. , Nikul’shin P.V. , Mezhenkova T.V.
An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol
Russian Chemical Bulletin. 2021. V.70. N5. P.995-998. DOI: 10.1007/s11172-021-3178-3 WOS Scopus РИНЦ

Третьяков Е.В. , Максимов А.М. , Никульшин П.В. , Меженкова Т.В.
Эффективный подход к синтезу 2,3,4,5-тетрафторфенола
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2021. Т.70. №5. С.995-998. РИНЦ

Published print:	May 1, 2021
Published online:	Jun 2, 2021

Web of science	WOS:000657311100026
Scopus	2-s2.0-85107131420
Elibrary	46800318
OpenAlex	W3168264073