Optimisation of the synthesis of 2-(aryl)-2-((hydroxyimino)thiophene-3(2H)-ylidene)-acetonitriles - precursors of non-ionic photoacid generators
V. A. KONOREV, A. M. AGAFONTSEV, E. V. VASILIEV, V. V. SHELKOVNIKOV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: photoacid generators, 2-nitrothiophene, vicarious nucleophilic substitution, arylacetic acid nitriles
Abstract
For developing a convenient method to synthesise 2-(aryl)-2-((hydroxyimino)thiophene-3(2H)-ylidene)-acetonitriles, which are the key intermediates in the synthesis of non-ionic photoacid generators, the conditions for the condensation of 2-nitrothiophene with the nitriles of arylacetic acids have been optimised. It has been shown that this process is most favourable with the use of sodium methoxide in tetrahydrofuran with small additions of methanol. Under these conditions, benzyl cyanides react to form 2-(aryl)-2-((hydroxyimino)thiophene-3(2H)-ylidene)-acetonitriles in the yields of 45-76 %.
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