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. SDS of cas: 21524-34-5
A 20 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 2-bromo-1,3,5-triisopropylbenzene (566 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h. 1-bromo-2-iodo-3,4-dimethoxybenzene (700 mg, 2.1 mmol) in anhydrous THF (3 mL) was injected through syringe. An additional 1 mL of THF was used to rinse the reaction and was also transferred into the mixture. The combined reaction mixture was stirred at 70 C. overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (1.3 g, 5 mmol) in 6 mL anhydrous THF was added drop-wise over 10 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (20 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (415 mg, 40%), labeled as 23MeOTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.41-7.31 (m, 4H), 7.27-7.23 (m, 1H), 7.20 (s, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.94 (d, J=8.3 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H), 2.76-2.66 (m, 1H), 2.51 (p, J=6.9 Hz, 1H), 2.38 (p, J=6.9 Hz, 1H), 1.26 (d, J=6.9 Hz, 3H), 1.13 (d, J=6.9 Hz, 6H), 1.08 (d, J=6.9 Hz, 3H), 1.04 (d, J=6.8 Hz, 3H), 0.80 (d, J=7.3 Hz, 3H), 0.76 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl3) delta 150.79, 148.74, 144.81, 143.30, 142.70, 142.16, 137.90, 131.47, 130.65, 127.18, 126.35, 126.27, 119.60, 119.38, 111.62, 60.37, 55.93, 32.28, 31.97, 30.58 (d), 29.79 (d), 25.09, 24.98, 24.32 (t), 23.58, 23.45 ppm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21524-34-5, 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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