Quality Control of 1,3-Dimethoxybenzene. In 2020 ANGEW CHEM INT EDIT published article about DIRECTED ORTHO-METALATION; SODIUM DIISOPROPYLAMIDE; ORGANOLITHIUM COMPOUNDS; ALKALI-METALS; STRONG BASES; LITHIUM; REARRANGEMENT; DERIVATIVES; ALKOXIDES; REAGENTS in [Harenberg, Johannes H.; Weidmann, Niels; Knochel, Paul] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany in 2020, Cited 60. The Name is 1,3-Dimethoxybenzene. Through research, I have a further understanding and discovery of 151-10-0.
We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 m in hexane) complexed with TMEDA (N,N,N ‘,N ‘-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between -78 degrees C and 25 degrees C with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min(-1) using a commercial flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.
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Reference:
Isothiazole – Wikipedia,
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