Reference of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.
In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96percent yield as an yellow oil. Ethyl 2-(1,1,2,2-tetrafluorobut-3-en-1-yl)benzoate (4j) Yield: 96percent (0.13 g, 0.48 mmol); Yellow oil (hexanes/AcOEt = 15/1, Rf = 0.29); 1H NMR (CDCl3): 1.35 (t, J = 7.1 Hz, 3H, CH2CH3), 4.36 (q, J = 7.1 Hz, 2H, CH2CH3), 5.70 (d, J = 11.0 Hz, 1H, trans-CH2CHCF2), 5.86 (dt, J = 17.3, 2.2 Hz, 1H, cis-CH2CHCF2), 6.07 (ddt, J = 17.3, 11.4, 11.0 Hz, 1H, CF2CH), 7.47?7.62 (m, 4H, ArH); 13C NMR (CDCl3): 14.1 (CH2CH3), 61.9 (CH2CH3), 115.2 (tt, J = 250.2, 37.2 Hz, CF2), 116.6 (tt, J = 253.4, 36.1 Hz, CF2), 124.2 (t, J = 9.3 Hz, CH2), 126.8 (t, J = 24.4 Hz, CF2CH), 127.7 (t, J = 24.5 Hz, Ar), 128.5 (Ar), 128.7?128.9 (m, Ar), 129.7(Ar), 131.1 (Ar), 133.8 (t, J = 3.3 Hz, Ar), 168.6 (C=O); 19F NMR (CDCl3): 106.44 (s, 2F, CF2Ar), 113.42 (d, J = 11.4 Hz, 2F, CF2CH); IR (neat): 3076, 2988, 2903, 1739, 1578, 1415, 1370, 1269, 1152 cm-1 ; HRMS (FAB) calcd for [M+H]+ C13H13F4O2: 277.0852, found 277.0847.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-iodobenzoate, 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;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com