材料科学。
医药; 农药; 塑料及橡胶添加剂; 消毒剂及防腐剂; 精细化学品
合成路线 1(1. 合成:14753-51-6)
产率:85%
合成条件:Stage #1: With sodium hydroxide In water Stage #2: With bromine; acetic acid In water at 20℃; for 12 h; Cooling with ice; Inert atmosphere
实验步骤:向装有氮气入口和气体出口的1L三颈烧瓶中加入氢醌(20g,182),该烧瓶连接到含有氢氧化钠水溶液(7.26g NaOH,在300mL水中)和滴液漏斗的鼓泡器中。 毫摩尔)在200毫升冰醋酸中。 将烧瓶置于冰浴中并开始氮气流动。 在20分钟内逐滴加入溴(60.9g,381mmol)。 在此期间,从溶液中沉淀出白色固体,然后在室温下搅拌反应混合物12小时。 在冰浴中冷却后,过滤反应内容物并用冷水洗涤至中性。 将白色固体产物1,4-二溴-2,5-二羟基苯(41.4g,85%)真空干燥。 1H NMR(300MHz,CDCl3):δ7.14(2H,s),5.2(2H,br,s)。
参考文献:
- [1] Journal of Chemical Research - Part S, 2002, # 6, p. 272 - 275 [2] Patent: US9981887, 2018, B1. Location in patent: Page/Page column 8 [3] Chemistry Letters, 1987, p. 627 - 630 [4] Journal of Materials Chemistry A, 2015, vol. 3, # 5, p. 1920 - 1924 [5] Chinese Journal of Chemistry, 2017, vol. 35, # 4, p. 447 - 456 [6] Chemistry - A European Journal, 2005, vol. 11, # 20, p. 5889 - 5898 [7] Macromolecules, 2006, vol. 39, # 24, p. 8303 - 8310 [8] Journal fur Praktische Chemie - Chemiker - Zeitung, 1996, vol. 338, # 4, p. 363 - 373 [9] Polymer, 2010, vol. 51, # 23, p. 5294 - 5303 [10] Journal of the American Chemical Society, 2014, vol. 136, # 50, p. 17434 - 17437 [11] Tetrahedron, 1997, vol. 53, # 30, p. 10357 - 10400 [12] Collection of Czechoslovak Chemical Communications, 2001, vol. 66, # 10, p. 1473 - 1489 [13] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 2938 - 2942 [14] Tetrahedron, 2011, vol. 67, # 18, p. 3175 - 3180 [15] Journal of the American Chemical Society, 2009, vol. 131, # 40, p. 14267 - 14273 [16] Advanced Functional Materials, 2010, vol. 20, # 22, p. 3847 - 3855 [17] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 10, p. 6920 - 6924 [18] Helvetica Chimica Acta, 1999, vol. 82, # 9, p. 1418 - 1422 [19] Journal of the American Chemical Society, 2008, vol. 130, # 14, p. 4699 - 4707 [20] Molecular Crystals and Liquid Crystals, 2010, vol. 519, p. 54 - 61 [21] Polymer, 2013, vol. 54, # 14, p. 3542 - 3547 [22] Monatshefte fuer Chemie, 1880, vol. 1, p. 360 [23] DRP/DRBP Org.Chem., [24] Macromolecules, 2004, vol. 37, # 20, p. 7451 - 7463 [25] Justus Liebigs Annalen der Chemie, 1881, vol. 209, p. 109 [26] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 91, p. 178 - 183 [27] Journal of Nanoscience and Nanotechnology, 2012, vol. 12, # 5, p. 4365 - 4369 [28] Dyes and Pigments, 2013, vol. 97, # 2, p. 318 - 323 [29] CrystEngComm, 2013, vol. 15, # 11, p. 2067 - 2075 [30] Chemical Communications, 2017, vol. 53, # 57, p. 8038 - 8041 [31] Organic Electronics: physics, materials, applications, 2019, vol. 64, p. 247 - 251
合成路线 2(2. 合成:14753-51-6)
产率:79%
合成条件:With boron tribromide In dichloromethane for 24 h; Reflux
实验步骤:在100ml单颈烧瓶中,加入7.1g(24.2mmol,1.0当量)1,4-二溴-2,5-二甲氧基苯和30ml二氯甲烷。 加入BGr3后加入4.6ml(49.6mmol,2.05eq),回流反应24h。 蒸馏出二氯甲烷,搅拌下加入50ml水。 将滤饼用水洗涤并用水洗涤。 真空干燥,得到5.08g白色固体,收率79%。
参考文献:
- [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 365, p. 481 - 489 [2] Journal of Materials Chemistry, 2011, vol. 21, # 28, p. 10472 - 10481 [3] Patent: CN106397468, 2017, A. Location in patent: Paragraph 0012; 0019 [4] Monatshefte fuer Chemie, 1924, vol. 45, p. 578 [5] Macromolecules, 2002, vol. 35, # 13, p. 4975 - 4982