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: 1573-9171 , E-ISSN: 1066-5285

Output data

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

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

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 OpenAlex

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

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