27993-58-4Relevant academic research and scientific papers
Phase transfer catalyst in grindstone synthesis of 3-oxopropanenitrile: One pot synthesis of polysubstituted amino thiophenes
Patil, Shivaraj P.,Kanawade, Shrikant B.,Shinde, Madhukar P.,Toche, Raghunath B.
, p. 33 - 36 (2013/09/24)
The chemoselective SN2 reaction of ω-bromoacetophenone with sodium cyanide or potassium cyanide in DMF-water or in biphasic solvent toluene-water using tetrabutylammonium bromide (TBAB) as phase-transfer catalyst, performed by grinding, furnished 3-oxopropanenitriles 2 as the sole product in 70-80% yield, while in ethanolwater, mixture of compound 2 and oxirane 3 were obtained. The obtained 3-oxopropanenitriles 2 were used for one pot synthesis of 2-amino-3-carbonitrile thiophenes.
Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones
Fuglseth, Erik,Thvedt, Thor H?kon Krane,M?ll, Maria F?rde,Hoff, B?rd Helge
, p. 7318 - 7323 (2008/12/21)
para-Substituted α-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of α-fluoroacetophenones and the corresponding 2-fluoro-1,1-dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of α-bromoacetophenones using tetrabutylammonium hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced.
