Synlett

Synthesis of O, O-diethyl arylthiophosphonate from O-Aryl-O, O-diethylthiophosphate

T Dieng, A Fraix, JY Salaün, I Dez, RJMK Gebbink…

Index: Dieng, Thierno; Fraix, Aurore; Salauen, Jean-Yves; Dez, Isabelle; Klein Gebbink, Robertus J. M.; Van Koten, Gerard; Jaffres, Paul-Alain Synlett, 2008 , # 20 p. 3121 - 3124

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Abstract

With the aim to improve the efficiency of the orthometallation of substrate 1a, t-BuLi was used to perform the reaction (Table [¹] , entry 4). The conversion was indeed increased but the yield stayed quite modest (48%). Finally, a metal-halogen exchange performed by reaction of n-BuLi with 1b (Table [¹] entry 5) allowed us to observe a full conversion of the substrate affording the pure arylthiophosphonate 2 in good yield (95%). A ³¹ P NMR monitoring of this reaction ...