化学合成。
医药; 香料; 染料
合成路线 1(1. 合成:2316-64-5)
产率:84%
合成条件:With sodium tetrahydroborate In ethanol at 0 - 20℃; for 18 h; Schlenk technique; Inert atmosphere
实验步骤:根据文献使用改进的合成方法制备化合物:在0℃下,将5-溴-2-羟基苯甲醛(10.1g,50mmol)溶解在250mL乙醇中。 将NaBH 4(1.88g,50mmol)分批(0.3g)加入到搅拌的溶液中。 将混合物在室温下搅拌18小时。 在减压(10 2毫巴)下除去乙醇后,将得到的浅黄色固体溶于200mL饱和NH 4 Cl水溶液中。 将粗产物用乙醚(三次80mL)萃取。 将有机相用盐水洗涤(三次,20mL)并用MgSO 4干燥2小时。 通过过滤除去MgSO 4并在减压(10 2 mbar)下过量溶剂后,通过快速色谱法用二氧化硅(洗脱液:正己烷/乙酸乙酯 - 体积比为8/2)纯化产物,蒸发后得到无色固体。 溶剂(8.52克,84%);
参考文献:
- [1] Tetrahedron Asymmetry, 2011, vol. 22, # 13, p. 1395 - 1399 [2] Journal of Chemical Research - Part S, 2003, # 6, p. 335 - 339 [3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2003, vol. 58, # 12, p. 1220 - 1226 [4] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 2, p. 307 - 315 [5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 4, p. 453 - 457 [6] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 2, p. 317 - 326 [7] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2004, vol. 59, # 6, p. 704 - 710 [8] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 6-7, p. 861 - 864 [9] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1658 - 1667 [10] Inorganica Chimica Acta, 2014, vol. 409, # PART B, p. 472 - 478 [11] Journal of Materials Chemistry A, 2016, vol. 4, # 7, p. 2705 - 2719 [12] Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 6761 - 6764 [13] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 2910 - 2917 [14] Acta Chemica Scandinavica (1947-1973), 1965, vol. 19, p. 255 - 256 [15] Journal of Physical Chemistry, 1984, vol. 88, # 9, p. 1913 - 1916 [16] Tetrahedron, 1999, vol. 55, # 2, p. 433 - 448 [17] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 10-12, p. 1325 - 1328 [18] ChemMedChem, 2013, vol. 8, # 6, p. 956 - 966 [19] Organic and Biomolecular Chemistry, 2013, vol. 11, # 45, p. 7838 - 7842 [20] Chemical Communications, 2014, vol. 50, # 56, p. 7531 - 7534 [21] Patent: WO2014/130608, 2014, A1. Location in patent: Page/Page column 102 [22] Organic Letters, 2015, vol. 17, # 19, p. 4790 - 4793 [23] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 9, p. 2308 - 2313 [24] European Journal of Organic Chemistry, 2016, vol. 2016, # 28, p. 4824 - 4833 [25] Patent: CN107188813, 2017, A. Location in patent: Paragraph 0054; 0065-0066 [26] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4246 - 4251