A common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, its 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. 22385-77-9.
Compound 9 (12.2 g, 24.5 mmol) was dissolved in THF (100 mL) and cooled to -78 ¡ãC. To thissolution was added at -78 ¡ãC a freshly prepared solution of LDA from diisopropylamine (5.15 mL, 36.7mmol) and n-BuLi (22.2 mL, 1.65 M, 36.7mmol) in THF (50 mL). After stirring at -78 ¡ãC for 30 min, the resulting solution was added to asuspension of ZnCl2 (12.1 g, 89.1mmol) in THF (100 mL) at -78 ¡ãC. The reaction mixture was stirred at -78 ¡ãC for 1 h and warmed to room temperature, where stirring was continued for 1 h. The resulting solution was added to a solution of 1-bromo-3,5-di-t-butylbenzene (6.60 g, 24.5mmol) and [Pd(PPh3)4] (1.42 g, 1.22 mmol) in THF (50 mL). The resulting solution was heated at 60 ¡ãC for 10 h, before the reaction was quenched by addition of saturated aqueous sodium hydrogen carbonate. The reaction mixture was extracted with Et2O and the combined organic phases were washed with water and dried over MgSO4. After filtration and evaporation of all volatiles under reduced pressure, the obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1) to give10 (13.5 g, 19.7mmol, 80percent).
The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.
Reference:
Article; Sakagami, Michiyasu; Sasamori, Takahiro; Sakai, Heisuke; Furukawa, Yukio; Tokitoh, Norihiro; Bulletin of the Chemical Society of Japan; vol. 86; 10; (2013); p. 1132 – 1143;,
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