Some common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, 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. 766-46-1
For the synthesis of 1e, the title compound 1e? wasprepared as follows. A solution of LDA, prepared from iPr2NH(0.93 mL, 6.5 mmol) and nBuLi (2.7M in hexane, 2.4 mL, 6.5 mmol)in THF (6 mL) at 0 C, was added to a solution of 1-bromo-2-ethynylbenzene [766-46-1] (1.1 g, 5.9 mmol) in THF (6 mL)at 78 C for 30 min tert-Butyldimetylsilyl chloride [18162-48-6](1.1 g, 7.1 mmol) was added to the mixture at that temperature.The reaction mixturewas warmed to room temperature and stirredfor 12 h. After adding aqueous NH4Cl, the aqueous mixture wasextracted with hexane three times. The combined organic phasewas dried over Na2SO4 and evaporated. Purification of the residueby silica-gel column chromatography gave 1-bromo-2-[2-[(1,1-dimethylethyl)dimethyl-silyl]ethynyl]benzene in (1.6 g, 5.4 mmol,92%) as a pale yellow liquid. 1H NMR (400 MHz, CDCl3, 7.26 ppm)d 0.21 (s, 6H), 1.02 (s, 9H), 7.15 (ddd, J 7.6, 7.6, 1.6 Hz, 1H), 7.24(ddd, J 7.6, 7.6, 1.2 Hz, 1H), 7.50 (dd, J 7.6, 1.6 Hz, 1H), 7.57 (dd,J 8.0, 1.2 Hz, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 766-46-1, its application will become more common.
Reference:
Article; Kinoshita, Hidenori; Fukumoto, Hiroki; Ueda, Akihiro; Miura, Katsukiyo; Tetrahedron; vol. 74; 14; (2018); p. 1632 – 1645;,
Bromide – Wikipedia,
bromide – Wiktionary