Application of 5153-40-2,Some common heterocyclic compound, 5153-40-2, name is 1-Bromo-2,3,4,5,6-pentamethylbenzene, molecular formula is C11H15Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A solution of 15.92 g (80 mmol) 2,4,6-Me3C6H2Br in 80 mL THF was added dropwise to 2.32 g (96 mmol) Mg, activated with 3 g (16 mmol) 1,2-Br2C2H4, in 20 mL THF. The reaction mixture was refluxed for 2 h and afterward allowed to cool to r.t. To the Grignard reagent solution was added dropwise a solution of 7.55 g (16 mmol) 2,4,6-I3C6H2OH and0.44 g (0.64 mmol) [(IPr)PdCl2(3-ClC5H4N)]. The reaction mixture was refluxed for another 21 h and quenched with2 mL H2O stirring under argon for 30 min. After solvent removal, the obtained residue was dissolved in 80 mL Et2Oand 20 mL CH2Cl2 and filtered over a 2 cm alumina pad. Solvent removal at reduced pressure afforded a brown oil which was eluted over a 10 cm alumina column witha mixture of Et2O-pentane 2:1 (v/v). To the pale-yellow oil obtained after the solvent removal, methanol was added. After sonication, 1 precipitated as a colorless solid. Filtration and vacuum drying afforded 3.8 g (52 %) of 1.
The synthetic route of 5153-40-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; olea, Atena B.; Olaru, Marian; Silvestru, Cristian; Ra, Ciprian I.; Zeitschrift fur Naturforschung – Section B Journal of Chemical Sciences; vol. 70; 1; (2015); p. 77 – 81;,
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