Abstract
Electrolytic partial fluorination of ethyl α-2-(pyrimidylthio)acetate was comparatively studied in acetonitrile and 1,2-dimethoxyethane (DME) containing Et 4NF ·4HF as a supporting electrolyte and a fluoride ion source. Acetontrile was not suitable for the fluorination due to the severe anode passivation. In contrast, use of DME provided the corresponding α-monofluorinated product in quantitative yield. A mixed electrolytic solvent of DME and acetonitrile was also effective for the fluorination and the product yield increased with an increase of the ratio of DME to acetonitrile. The superiority of DME can be explained mainly in terms of both the suppression of the anode passivation and enhancement of the nucleophilicity of fluoride ions.
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