1578-63-8Relevant articles and documents
FURTHER STUDIES ON THE SYNTHESIS OF α-FLUORO CARBONYL COMPOUNDS
Cantrell, Gary L.,Filler, Robert
, p. 35 - 46 (1985)
The trimethylsilyl enol ethers of cycloalkanones and acid esters are converted in high yields (70-90percent) to the corresponding α-fluoro carbonyl derivative using XeF2 in CH2Cl2.Non-cyclic α-hydroxy ketones such as ethyl mandelate are efficiently transformed to the α-fluoro product by DAST and by Ishikawa's reagent.Nucleophilic displacement of halogen by fluoride failed in cyclic systems, giving instead, α,β-unsaturated ketones in DMF or CH3CN (18-crown-6) and 1,2-diones in DMSO, with KF acting as a base.Attempts at DMSO oxidation of I(Br)F adducts failed to give the α-fluoro ketones, but resulted in dehydrohalogenation to the trans-vinyl fluorides.
Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride
Sap, Jeroen B. I.,Wilson, Thomas C.,Kee, Choon Wee,Straathof, Natan J.W.,Ende, Christopher W.am,Mukherjee, Paramita,Zhang, Lei,Genicot, Christophe,Gouverneur, Véronique
, p. 3237 - 3241 (2019/03/21)
Herein, we report the radiosynthesis of 18F-difluoromethylarenes via the assembly of three components, a boron reagent, ethyl bromofluoroacetate, and cyclotron-produced non-carrier added [18F]fluoride. The two key steps are a copper-catalysed cross-coupling reaction, and a Mn-mediated 18F-fluorodecarboxylation.
The effect of substituents and operating conditions on the electrochemical fluorination of alkyl phenylacetates in Et3N·4HF medium
Ilayaraja,Manivel,Velayutham,Noel
, p. 185 - 192 (2008/09/17)
Selective electrochemical fluorination of alkyl phenylacetates (Ph-CH2-COOR, where R is methyl, ethyl, n-propyl, n-butyl, i-propyl and sec-butyl) under galvanostatic conditions were reported in Et3N·4HF medium. Preparative electrolysis experiments were carried out both in pre-electrolysed dry Et3N·4HF and the same electrolyte medium without pre-electrolysis. Very little hydrolysed fluorinated products were obtained in pre-electrolysed medium where as significant quantities of hydrolysed products leading to fluorinated phenylacetic acid were obtained from Et3N·4HF without pre-electrolysis. Under optimum experimental conditions up to 87% selectivity of monofluoro ester could be achieved. Difluoro alkyl phenylacetate, monofluoro and difluoro phenylacetic acids were the other predominant side products obtained. The hydrolysis appears to be initiated by tautomeric transformation of proton after the initial electro oxidative formation of the cation radical. 19F as well as 1H NMR spectroscopy have been employed to identify the minor constituents formed during the electro oxidative process.
