Application of 16799-05-6,Some common heterocyclic compound, 16799-05-6, name is 3-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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 mixture of compound 3 or 4, R-X (3 equiv.) and Cs2CO3 (3 equiv.) in acetone/DMF (10 mL/10mL) was stirred at proper temperature (25-80C) for 20h. The reaction was quenched with water (30mL) and extracted with ethyl acetate (¡Á3). The organic layer was collected and washed with brine, and then dried over anhydrous MgSO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography.5.4.10 1-(3-Chlorophenethoxy)-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one (14) Following the general method, compound 3 (0.19 g, 0.06 mmol), 3-chloro-1-phenethyl bromide (0.30 g, 1.37 mmol) and K2CO3 (0.26 g, 1.85 mmol) were used at 80 C. The purification was conducted with eluent (ethyl acetate/n-hexane = 1:3) to give compound 14 (0.04 g, 15.4%) as a white solid. m.p. 146-148 C; Rf 0.63 (eluent: ethyl acetate/n-hexane = 1:1); HPLC: RT 4.05 min (condition A, purity: 98.2%); 1H NMR (CDCl3, 400 MHz) delta 2.78 (dd, J = 2.4, 4.8 Hz, 1H), 2.95 (t, J = 4.4 Hz, 1H), 3.28 (t, J = 7.2 Hz, 2H), 3.36-3.40 (m, 1H), 4.00 (dd, J = 7.0, 11.2 Hz, 1H), 4.25 (t, J = 7.2 Hz, 2H), 4.35 (dd, J = 2.8, 11.2 Hz, 1H), 6.35 (d, J = 2.4 Hz, 1H), 6.51 (d, J = 2.4 Hz, 1H), 7.20-7.38 (m, 5H), 7.43 (dd, J = 2.0, 2.0 Hz, 1H), 7.64 (ddd, J = 1.6, 7.2, 8.8 Hz, 1H), 8.31 (dd, J = 2.0, 8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 35.5, 44.8, 50.0, 69.4, 70.1, 94.0, 96.6, 108.1, 117.2, 123.4, 124.9, 127.0, 127.9, 129.6, 130.0, 133.9, 134.4, 140.3, 155.2, 159.2, 161.4, 163.7, 175.3, 175.4 ppm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chlorophenethyl Bromide, its application will become more common.
Reference:
Article; Park, Seojeong; Hong, Eunji; Kwak, Soo Yeon; Jun, Kyu-Yeon; Lee, Eung-Seok; Kwon, Youngjoo; Na, Younghwa; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 211 – 225;,
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