Harenberg, JH; Weidmann, N; Wiegand, AJ; Hoefer, CA; Annapureddy, RR; Knochel, P in [Harenberg, Johannes H.; Weidmann, Niels; Wiegand, Alexander J.; Hoefer, Carla A.; Annapureddy, Rajasekar Reddy; Knochel, Paul] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany published (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow in 2021, Cited 106. Recommanded Product: 151-10-0. The Name is 1,3-Dimethoxybenzene. Through research, I have a further understanding and discovery of 151-10-0.
We report the on-demand generation of hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be a very useful reagent and undergoes in-line Br/Na-exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb-amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale-up of the Br/Na-exchange using an in-line electrophile quench was also reported.
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