These common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, its 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. Application In Synthesis of Methyl 3-bromopropiolate
To a stirring solution of1,8-dihydroxynaphthalene (2) (1.74 g, 10.9 mmol) and methyl 3-bromopropiolate32 (2.65 g, 16.3 mmol)in anhydrous CH2Cl2 (40 mL) was added DABCO (2.66 g, 21.8 mmol) at 0 C under an argon atmosphere.After being stirred at room temperature for 3 h, the reaction mixture was treated with 1 M aqueous HCl.The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with brine,dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatographyeluting with 25% EtOAc/hexane to yield the title compound (2.17 g, 8.96 mmol, 82%) as a white solid. Rf0.34 (20% EtOAc/hexane). Mp 115-118 C. IR nu (neat, cm-1): 1721, 1654, 1602, 1419, 1381, 1281, 1248,1131, 1089, 815, 799, 753. 1H-NMR (400 MHz, CDCl3): delta 7.52 (d, J = 8.3 Hz, 1H), 7.51 (d, J = 8.3 Hz,1H), 7.45 (dd, J = 8.3, 7.6 Hz, 1H), 7.42 (dd, J = 8.3, 7.3 Hz, 1H), 7.13 (d, J = 7.3 Hz, 1H), 6.93 (d, J =7.6 Hz, 1H), 4.97 (s, 1H), 3.75 (s, 3H). 13C-NMR (100 MHz, CDCl3): delta 166.2, 158.6, 144.4, 144.1, 133.6,128.0, 127.8, 121.9, 121.7, 110.6, 108.4, 107.6, 78.2, 50.9. HRMS (ESI, [M+H]+): calcd for C14H11O4,243.0652; found, 243.0653
The synthetic route of Methyl 3-bromopropiolate has been constantly updated, and we look forward to future research findings.
Reference:
Article; Tsukamoto, Hirokazu; Nomura, Yumi; Doi, Takayuki; Heterocycles; vol. 99; 1; (2019); p. 549 – 565;,
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