Synthesis
The general procedure for the synthesis of 3'-bromophenylacetylene from (3-bromophenylethynyl)trimethylsilane was as follows: intermediate 1-1 (166 g, 655.6 mmol) was dissolved in methanol (1000 mL) and placed in the reactor. Subsequently, potassium carbonate (90.6 g, 655.6 mmol) was added slowly and dropwise to the above solution. The reaction mixture was stirred at room temperature for about 30 minutes and then filtered. The filtrate was distilled under reduced pressure to remove the solvent and the residue was dissolved in ethyl acetate. This ethyl acetate solution was washed twice with distilled water to remove water soluble impurities. Finally, the organic solvent was removed by reduced pressure distillation to give intermediates 1-2 (116 g, 98% yield).
References
[1] Patent: US2018/339967, 2018, A1. Location in patent: Paragraph 0159; 0161
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 630 - 639
[3] European Journal of Organic Chemistry, 2010, # 33, p. 6323 - 6330
[4] Organic Letters, 2017, vol. 19, # 19, p. 5182 - 5185
[5] Patent: US2009/48320, 2009, A1. Location in patent: Page/Page column 62; 82
