Application of 31930-34-4,Some common heterocyclic compound, 31930-34-4, name is Ethyl cis-3-Bromoacrylate, molecular formula is C5H7BrO2, 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 round-bottomed flask, at 0 C,were successively added Et3N (45 mL), F (5.25 g, 29 mmol), triisopropylsilylacetylene(6.5 mL, 29 mmol), PdCl2(PPh3)2 (330 mg, 0.5 mmol) and CuI (95 mg, 0.5 mmol). The mixture was stirred at 0 C for 4 h, then water (50 mL) was added. The crude was extracted with EtOAc(2 × 50 mL), washed with brine, dried over Na2SO4, filtered and concentrated in vacuum. After purification by chromatography on silica gel (cyclohexane/ethyl acetate 98:2), 6.6 g of an orange liquid were obtained (81% yield). 1H NMR (300 MHz, CDCl3) delta 6.14 (d, J = 11.7 Hz,1H), 6.05 (d, J = 11.7 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 1.27 (t, J = 7.1 Hz, 3H), 0.80-1.50 (m,21H). 13C NMR (126 MHz, CDCl3) delta 164.6, 129.4, 122.4, 105.1, 102.6, 60.5, 18.7, 14.4, 11.5. HRMS (ESI-TOF) m/z [M + Na]+ Calcd for C16H28NaO2Si 303.1751; Found 303.1764.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl cis-3-Bromoacrylate, its application will become more common.
Reference:
Article; Fuentespina, Ruben Pomar; De La Cruz, Jose Angel Garcia; Durin, Gabriel; Mamane, Victor; Weibel, Jean-Marc; Pale, Patrick; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1416 – 1424;,
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