Some common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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. Recommanded Product: 4-Bromo-3,3,4,4-tetrafluorobut-1-ene
In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil. 3,3,4,4-Tetrafluoro-4-phenylbut-1-ene (4a) [S1] Known compound; Yield: 29% (0.036 g, 0.17 mmol); Colorless oil (hexanes, Rf = 0.57); 1H NMR (CDCl3): 5.69 (d, J = 11.6 Hz, 1H, trans-CH2CHCF2), 5.83 (dt, J = 17.2, 1.6 Hz, 1H, cisCH2CHCF2), 6.02 (ddt, J = 17.2, 11.6, 11.5 Hz, 1H, CF2CH), 7.44-7.58 (m, 5H, ArH); 13C NMR (CDCl3): 115.1 (tt, J = 248.8, 37.2 Hz, CF2), 116.4 (tt, J = 252.1, 35.5 Hz, CF2), 124.1 (t, J = 9.9Hz, CH2), 126.7 (t, J = 24.8 Hz, CF2CH), 126.9 (td, J = 6.6, 1.7 Hz, Ar), 127.0-127.7 (m, Ar), 128.2 (Ar), 131.0 (t, J = 1.7 Hz, Ar); 19F NMR (CDCl3): 112.56 (s, 2F, CF2Ar), 114.95 (d, J = 11.46 Hz, 2F, CF2CH); IR (neat): 3071, 1653, 1424, 1286, 1243, 1130, 1070, 949 cm-1 ; HRMS (FAB) calcd for [M]+ C10H8F4: 204.0562, found 204.0558.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18599-22-9, its application will become more common.
Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
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