四-(4-溴苯)乙烯为烯烃类有机物,可用作有机合成中间体。制备方法包括:(1)回流:在250mL双口烧瓶中加入四苯乙烯,注入溴水,搅拌并点板跟踪;(2)点板:用THF稀释反应混合物,石油醚-二氯甲烷(20∶1)作展开剂;(3)除溴:改装回流装置,加甲苯除溴蒸气;(4)浓缩:旋蒸至20mL;(5)色谱分离:石油醚-二氯甲烷(20∶1)作展开剂分离;(6)旋蒸:收集组分旋蒸得白色固体;(7)烘干:70℃烘干24h。反应物物料比1∶10、反应时间16h时产率最高。
有机合成中间体
合成路线 1(1. 合成:61326-44-1)
- 步骤:将75mmol(25G)1,1,2,2-四苯基乙烯置于干燥器架上的表玻璃中,将585mmol(30ml)溴化物液体倒入干燥器底部,用小孔封闭干燥器释放HBr,7天后收集黄色固体,用二氯甲烷/甲醇(2:1)重结晶得白色晶体。
- 条件:for 168 h(注:此处原文献条件可能存在笔误,实验步骤中反应时间为7天);
- 收率:37g,76%。
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合成路线 2(2. 合成:61326-44-1)
- 步骤:在0℃下,氩气氛围中向粉末锌(2.15g,33mmol)的无水THF(40mL)悬浮液中滴加氯化钛(IV)(1.81mL,16.5mmol),混合物回流4小时后冷却至室温;加入(4-溴苯基)苯基甲酮(980mg,4.12mmol)和4,4'-二甲氧基二苯甲酮(1.0g,4.12mmol)的THF(70mL)溶液,加热回流5小时;冷却后用10%K₂CO₃水溶液(100mL)淬灭,真空过滤除去不溶物,水层用CH₂Cl₂(3×50mL)萃取,合并有机层用水(20mL)洗涤,Na₂SO₄干燥,减压除溶剂,柱色谱(硅胶/乙酸乙酯:石油醚1:5)纯化得浅黄色固体。
- 条件:With titanium tetrachloride; zinc In tetrahydrofuran; Reflux; Inert atmosphere;
- 收率:776mg,40%。
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