methyl-3-(4-bromophenyl)-2-chloro propanoate | 14437-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl-3-(4-bromophenyl)-2-chloro propanoate
• 英文别名: 3-(4-Bromo-phenyl)-2-chloro-propionic acid methyl ester；Methyl 3-(4-bromophenyl)-2-chloropropanoate
• CAS: 14437-34-4
• 化学式: C₁₀H₁₀BrClO₂
• 分子量: 277.545
• InChiKey: HLARDTPGBDAKJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 di(4-bromophenyl)iodonium triflate 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 [Cu(dpp)₂]PF₆ 、 potassium chloride 、 2-methyl-N-(pyridin-2-ylmethylene)propan-2-amine 作用下， 以 乙腈 为溶剂， 以72 %的产率得到methyl-3-(4-bromophenyl)-2-chloro propanoate
  参考文献：
  名称：

  A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes

  摘要：

  Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.

  DOI：

  10.1002/anie.202405939