7511-49-1 1,3,5-三(4-溴苯基)苯

该物质属于可燃固体（存储类别11），具有严重眼损伤（类别1），对水生环境有长期危害（类别4）。需避免接触眼睛，采取防护措施（P280），若接触眼睛应立即用大量水冲洗（P305+P351+P338），并注意水生环境长期保护。

1,3,5-三(4-溴苯基)苯是一种有用的研究化学品，可用作有机中间体。

实验室研发过程中；化工医药合成过程中

合成路线 1（1. 合成：7511-49-1）

• 步骤：在装有冷凝器的圆底烧瓶中，将芳基烷基酮（3mmol）和硫酸化钨酸盐（20wt％）的混合物在130℃下搅拌，通过TLC监测反应进程。芳基烷基酮消失后，继续反应2小时。冷却反应混合物，用30mL乙酸乙酯稀释并过滤以回收催化剂。将滤液用10mL水洗涤，用硫酸钠干燥并减压浓缩。残余物通过硅胶（60-120）柱色谱纯化，用（PE：EA = 9：1）作为洗脱剂，得到纯的1,3,5-芳基苯。
• 条件：With sulfated tungstate In neat (no solvent) at 130℃; for 10 h
• 产率：84%
• 参考文献：[1] Synthetic Communications, 2013, vol. 43, #16, p.2178-2190；[2] RSC Advances, 2015, vol.5, #27, p.21206-21214；[3] Journal of the Iranian Chemical Society, 2012, vol.9, #5, p.791-798；[4] European Journal of Organic Chemistry, 2014, vol.2014, #14, p.2907-2916；[5] Synthetic Communications, 2005, vol.35, #24, p.3167-3171；[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol.45, #12, p.2781-2783；[7] Chemistry - A European Journal, 2012, vol.18, #20, p.6172-6182；[8] RSC Advances, 2016, vol.6, #60, p.55319-55326；[9] Polyhedron, 2012, vol.31, #1, p.721-728；[10] Tetrahedron Letters, 2017, vol.58, #31, p.3032-3036；[11] Chemical Communications, 2018, vol.54, #81, p.11475-11478；[12] Synthetic Communications, 2012, vol.42, #24, p.3569-3578；[13] RSC Advances, 2015, vol.5, #15, p.10869-10877；[14] Journal of the American Chemical Society, 2017, vol.139, #5, p.2053-2059；[15] Journal of Materials Chemistry, 2002, vol.12, #2, p.206-212；[16] Green Chemistry, 2010, vol.12, #8, p.1370-1372；[17] Journal of the Chemical Society, Perkin Transactions 1, 2000, #16, p.2695-2701；[18] Journal of Chemical Research, 2007, #12, p.720-721；[19] New Journal of Chemistry, 2002, vol.26, #3, p.291-297；[20] Advanced Synthesis and Catalysis, 2013, vol.355, #5, p.957-972；[21] Chemistry - A European Journal, 2015, vol.21, #51, p.18576-18579；[22] RSC Advances, 2016, vol.6, #102, p.100195-100202；[23] Tetrahedron Letters, 1991, vol.32, #33, p.4175-4176；[24] European Journal of Organic Chemistry, 2004, #19, p.4003-4013；[25] European Journal of Organic Chemistry, 2008, #18, p.3129-3140；[26] Comptes Rendus Chimie, 2013, vol.16, #3, p.252-256；[27] Journal of Chemical Research - Part S, 2003, #12, p.778-779；[28] Synlett, 2008, #15, p.2365-2367；[29] Synthetic Communications, 2009, vol.39, #22, p.4117-4121；[30] RSC Advances, 2013, vol.3, #6, p.1902-1915；[31] Tetrahedron Letters, 2012, vol.53, #19, p.2436-2439；[32] Tetrahedron Letters, 2018, vol.59, #11, p.1023-1027；[33] Chemical Communications, 2014, vol.50, #43, p.5737-5740；[34] Journal of Materials Chemistry C, 2015, vol.3, #7, p.1582-1587；[35] Macromolecules, 2003, vol.36, #22, p.8353-8360；[36] Tetrahedron Letters, 2009, vol.50, #30, p.4335-4339；[37] Inorganic Chemistry, 2013, vol.52, #13, p.7311-7313；[38] Journal of Organic Chemistry, 2004, vol.69, #18, p.6050-6058；[39] Chemistry of Materials, 2017, vol.29, #24, p.10469-10477；[40] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p.1251-1258；[41] Journal of the American Chemical Society, 1953, vol.75, p.5959；[42] Tetrahedron Letters, 2005, vol.46, #46, p.7871-7875；[43] Journal of Materials Chemistry, 2011, vol.21, #34, p.12958-12963；[44] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2011, vol.71, #1-2, p.113-120；[45] Journal of Materials Chemistry, 2012, vol.22, #10, p.4502-4510；[46] Patent: EP2586766, 2013, A1. Location in patent: Paragraph 0085；[47] CrystEngComm, 2016, vol.18, #42, p.8147-8150；[48] Angewandte Chemie - International Edition, 2016, vol.55, #47, p.14614-14617；[49] Angew. Chem., 2016, vol.128, p.14834-14837,4；[50] Chemistry - A European Journal, 2018, vol.24, #18, p.4547-4551

合成路线 2（3. 合成：7511-49-1）

• 步骤：将4-溴苯乙酮（7.962g，40mmol）和原甲酸乙酯（8mL，48mmol）溶解在烧瓶中的苯（24mL）中。在室温和搅拌下将气态氯化氢鼓泡通过溶液3小时。溶液变成棕红色，在第一个小时内开始形成沉淀。滤出所得沉淀物，用丙酮和甲醇洗涤，并干燥。从氯仿中重结晶的产物。
• 条件：With hydrogenchloride In benzene at 20℃; for 3 h
• 产率：43.6%
• 验证：合成产物的1H NMR光谱（500MHz），δ：7.68（s，3H）；7.60（d，6 H，J = 8.5 Hz）；7.53（d，6 H，J = 8.5 Hz）完全对应于1,3,5-三（4-溴苯基）苯的1H NMR光谱。
• 参考文献：[1] Russian Chemical Bulletin, 2018, vol.67, #8, p.1433-1439；[2] Izv. Akad. Nauk, Ser. Khim., 2018, #8, p.1433-1439,7