Synthetic Route of 21524-34-5,Some common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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.
To a 50 mL oven-dried flask was added 2-bromo-1,3,5-triisopropylbenzene (10.14 g, 0.036 mol, 1.0 equiv.), phenyl boronic acid (7.32 g, 0.06 mol, 1.6 equiv.), K3PO4 (17.0 g, 0.80 mol, 2.2 equiv), Pd2(dba)3 (0.366 g, 0.4 mmol) and SPhos (0.328 g, 0.8 mmol). The flask was evacuated and back-filled with argon three times prior to 40 mL of dry THF and 40 mL of dry toluene was added via syringe. The mixture was then stirred and heated in a 100 C. oil bath for 16 hr. Upon reaction completion, as determined by GC-MS, the mixture was filtered through silica and washed with EtOAc. The filtrate was collected and the solvent was removed under vacuum. The crude residue was purified by flash chromatography on silica gel using an EtOAc/hexanes mixture (0 to 10% EtOAc) as the eluent to get a white solid (9 g, 90%). 1H NMR (600 MHz, Chloroform-d) delta 7.42 (dd, J=8.1, 6.8 Hz, 2H), 7.39-7.34 (m, 1H), 7.23-7.19 (m, 2H), 7.09 (s, 1H), 2.97 (p, J=7.0 Hz, 1H), 2.62 (ddd, J=12.7, 7.7, 6.4 Hz, 2H), 1.34 (dd, J=7.0, 0.9 Hz, 5H), 1.11 (dd, J=6.9, 0.9 Hz, 11H) ppm. 13C NMR (151 MHz, CDCl3) delta 147.82, 146.51, 140.84, 137.08, 129.80, 127.91, 126.40, 120.53, 77.26, 77.05, 76.84, 34.28, 30.28, 24.25, 24.13 ppm
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3,5-triisopropylbenzene, its application will become more common.
Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
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