2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪为有机化合物,可用作医药中间体和有机合成中间体,主要用于实验室研发和化工医药合成过程中。
医药; 有机合成
路线1:
- 步骤: 在氮气氛下,将50g(187mmol)2-氯-4,6-二苯基-1,3,5-三嗪溶于1L四氢呋喃(THF)中,加入45g(224.12mmol)(3-溴苯基)硼酸盐和2.1g(1.87mmol)四(三苯基膦)钯,搅拌混合物。随后加入64g(467mmol)碳酸钾饱和水溶液,加热回流80小时。反应完成后,加水,用二氯甲烷(DCM)萃取,无水MgSO₄除水,过滤减压浓缩,快速柱色谱分离纯化得到69g(95%)产物。
- 条件: With tetrakis(triphenylphosphine) palladium (0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12 h; Inert atmosphere
- 产率: 95%
- 参考文献: [1] Patent: CN105566200, 2016, A. Location in patent: Paragraph 0326; 0327; 0328; 0329 [2] Patent: US2017/84845, 2017, A1. Location in patent: Paragraph 0197-0200 [3] Patent: KR2017/11338, 2017, A. Location in patent: Paragraph 0390; 0392-0395 [4] Patent: US2017/222158, 2017, A1. Location in patent: Paragraph 0132; 0133; 0134; 0135 [5] Patent: US2017/331067, 2017, A1. Location in patent: Paragraph 0184-0187 [6] Patent: CN108409730, 2018, A. Location in patent: Paragraph 0054; 0058; 0059; 0060 [7] Patent: KR2015/59395, 2015, A. Location in patent: Paragraph 0168; 0169; 0170; 0171
路线2:
- 步骤: 将化合物10-1(1.5g,5.9mmol)、盐酸苄脒(2.0g,13.0mmol)和NaOH(0.5g,13.0mmol)加入乙醇(20ml)中,回流12小时,用水和乙醇洗涤得到1.7g(74%)产物。
- 条件: With sodium hydroxide; In ethanol; for 12 h; Reflux
- 产率: 74%
- 参考文献: [1] Patent: KR2017/79348, 2017, A. Location in patent: Paragraph 0198; 0203-0206 [2] Patent: EP2415769, 2012, A1. Location in patent: Page/Page column 118-119 [3] Patent: US9966541, 2018, B2. Location in patent: Page/Page column 97 [4] Patent: JP2018/90561, 2018, A. Location in patent: Paragraph 0066
路线3:
- 步骤: 100ml三口瓶中加入M-溴苯甲醛(10.8mmol,2g)、盐酸苯醌(21.6mmol,3.8g)、Na₂CO₃(21.6mmol,2.2g)、Ni(OAc)₂(1.08mmol,0.27g),加入50g甲苯,控制反应在110℃搅拌30小时。过滤,洗涤,无水乙醇重结晶,滤饼真空干燥得到3.6g(83%)产物。
- 条件: With nickel diacetate; sodium carbonate; In toluene; at 110℃; for 30 h;
- 产率: 83%
- 参考文献: [1] Patent: CN108264490, 2018, A. Location in patent: Paragraph 0068; 0069; 0070; 0071 [2] Journal of Fluorescence, 2018, vol. 28, # 2, p. 707 - 723
路线4:
- 步骤: 在氮气保护下,双颈烧瓶中加入3-溴苯甲酰氯(11.0 mmol, 2.41 g)、苯甲腈(22.0 mmol, 2.27 g)及15 mL二氯甲烷,冰浴冷却(0至5℃)搅拌30分钟。缓慢滴加氯化锑(11.0 mmol, 3.30 g),室温搅拌1小时,加热回流反应12小时。冷却至室温,抽滤收集黄色固体,真空干燥。将黄色固体溶于75 mL冰浴冷却(0至5℃)的28%氨水溶液中,搅拌30分钟,室温继续搅拌3小时,抽滤收集白色固体,水洗后真空干燥。将白色固体加入预热至155℃的30 mL N,N-二甲基甲酰胺中,搅拌10分钟后抽滤除不溶物,重复纯化步骤两次,加热减压蒸馏除去N,N-二甲基甲酰胺得到目标产物2.85 g(66.7%)。
- 条件: With antimony(III) chloride; In dichloromethane; at 0-5℃; for 30 min; Reflux; at 155℃; for 10 min; Inert atmosphere
- 产率: 66.7%
- 参考文献: [2] Journal of Materials Chemistry C, 2018, vol. 6, # 34, p. 9049 - 9054