250690-55-2Relevant articles and documents
Electrolytic partial fluorination of organic compounds. 35. Anodic fluorination of 2-pyrimidyl, 2-pyridyl, and 2-quinazolinonyl sulfides
Dawood, Kamal M.,Higashiya, Seiichiro,Hou, Yankun,Fuchigami, Toshio
, p. 7935 - 7939 (1999)
Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron-withdrawing group (EWG) at the position α to the sulfur atom was successfully carried out using Et4NF·nHF (n = 3, 4) or Et3N·3HF as a supporting electrolyte and a fluoride ion source in 1,2- dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2- (fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with α,α-difluorinated product. In contrast, the corresponding 2- quinazolinonyl sulfides underwent similarly α-fluorination along with unexpected ipso-fluorination through anodic desulfurization.
