Thorsten Meier , Sabine Lorenzen , Tanja Knuplez , Tobias Preitschopf , Karsten Koppe , Peter Barthen , Rüdiger Bertermann , Michael Schulte , Nikolai Ignat‘ev , Maik Finze
{"title":"2-Trifluoromethoxyacetic acid – Synthesis and characterization","authors":"Thorsten Meier , Sabine Lorenzen , Tanja Knuplez , Tobias Preitschopf , Karsten Koppe , Peter Barthen , Rüdiger Bertermann , Michael Schulte , Nikolai Ignat‘ev , Maik Finze","doi":"10.1016/j.jfluchem.2025.110396","DOIUrl":null,"url":null,"abstract":"<div><div>A straightforward and high-yield synthesis of 2-trifluoromethoxyacetic acid CF<sub>3</sub>OCH<sub>2</sub>C(O)OH starting from trifluoromethyl triflate CF<sub>3</sub>SO<sub>2</sub>OCF<sub>3</sub> is described. The trifluoromethoxide anion was generated from trifluoromethyl triflate and a fluoride source followed by a nucleophilic substitution reaction with the {OCF<sub>3</sub>}<sup>–</sup> ion to yield CF<sub>3</sub>OCH<sub>2</sub>C(O)OC<sub>2</sub>H<sub>5</sub>. The ester was converted into M{CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>} (M = Na, K) and the acid CF<sub>3</sub>OCH<sub>2</sub>C(O)OH was obtained from the sodium salt and HCl. In addition, the silver(I) salt of the {CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>}<sup>–</sup> anion was synthesized from CF<sub>3</sub>OCH<sub>2</sub>C(O)OH and silver(I) oxide. The study includes a new synthesis for the starting compound CF<sub>3</sub>SO<sub>2</sub>OCF<sub>3</sub> and a detailed description for the preparation of [N(CH<sub>3</sub>)<sub>4</sub>]{OCF<sub>3</sub>}. Furthermore, the crystal structures of CF<sub>3</sub>OCH<sub>2</sub>C(O)OH, CF<sub>3</sub>OCH<sub>2</sub>C(O)OC<sub>2</sub>H<sub>5</sub>, M{CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>} (M = K, Ag), and [N(CH<sub>3</sub>)<sub>4</sub>]{OCF<sub>3</sub>} are reported.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"282 ","pages":"Article 110396"},"PeriodicalIF":1.7000,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Fluorine Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022113925000089","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
A straightforward and high-yield synthesis of 2-trifluoromethoxyacetic acid CF3OCH2C(O)OH starting from trifluoromethyl triflate CF3SO2OCF3 is described. The trifluoromethoxide anion was generated from trifluoromethyl triflate and a fluoride source followed by a nucleophilic substitution reaction with the {OCF3}– ion to yield CF3OCH2C(O)OC2H5. The ester was converted into M{CF3OCH2CO2} (M = Na, K) and the acid CF3OCH2C(O)OH was obtained from the sodium salt and HCl. In addition, the silver(I) salt of the {CF3OCH2CO2}– anion was synthesized from CF3OCH2C(O)OH and silver(I) oxide. The study includes a new synthesis for the starting compound CF3SO2OCF3 and a detailed description for the preparation of [N(CH3)4]{OCF3}. Furthermore, the crystal structures of CF3OCH2C(O)OH, CF3OCH2C(O)OC2H5, M{CF3OCH2CO2} (M = K, Ag), and [N(CH3)4]{OCF3} are reported.
期刊介绍:
The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature.
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