Direct electrophilic fluorination of naproxen with NF-reagents

被引：10

作者：

Borodkin, Gennady I. ^{[1
,2
]}

Elanov, Innokenty R. ^{[1
]}

Gatilov, Yury V. ^{[1
]}

Shubin, Vyacheslav G. ^{[1
]}

机构：

[1] NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, 2 Pirogov St, Novosibirsk 630090, Russia

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2019年 / 228卷

关键词：

NF-reagent; Naproxen; Mechanism of fluorination; X-ray analysis; DISCOVERY;

D O I：

10.1016/j.jfluchem.2019.109412

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor (TM), F-TEDA-BF4) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H2O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.

引用

页数：6

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