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ω,ω-二溴对苯基苯乙酮的合成

Synthesis of ω,ω-Dibromo-p-phenyl Acetophenone
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摘要 以联苯、乙酰氯、溴素为原料,合成了ω,ω-二溴对苯基苯乙酮。首先,联苯和乙酰氯反应生成对苯基苯乙酮,收率88.0%;然后,对苯基苯乙酮以乙醇为反应介质,经溴素溴化合成ω,ω-二溴对苯基苯乙酮。重点探讨了溴化过程中原料摩尔比、反应温度、反应时间等因素对反应收率的影响。最佳反应条件为:n(溴素)∶n(对苯基苯乙酮)=2.2∶1,反应温度45-50℃,反应时间2.5 h,总收率达89.7%。产物熔点114-116℃。用元素分析、傅立叶变换红外光谱(FTIR)和核磁共振氢谱(1HNMR)确定了目标化合物的结构。研究结果为工业开发实验提供了依据。 ω,ω-Dibromo-p-phenyl acetophenone was synthesized from biphenyl,acetyl chloride and bromine.Firstly the reaction of biphenyl and acetyl chloride gave the p-phenyl acetophenone and its yield was close to 88.0%.Then,ω,ω-dibromo-p-phenyl acetophenone was obtained by bromination by the reaction of p-phenyl acetophenone using ethanol as the reaction medium.The effects of the reaction material ratio,temperature and time on the yield of the product were investigated.The optimal reaction conditions were obtained: ratio of bromine to p-phenyl acetophenone 2.2∶1,the reaction temperature ranges from 45~50 ℃ the reaction time 2.5 h.The yield under this optimum reaction conditions was up to 89.7%.m.p.114~116 ℃.The structure of the target product was confirmed by elementary analysis,FTIR and 1HNMR.The experimental results provide the important basic data for the industrial development of this product.
作者 赵宙兴 李政
出处 《精细化工》 EI CAS CSCD 北大核心 2010年第1期93-96,共4页 Fine Chemicals
基金 国家自然科学基金项目(20772096)~~
关键词 对苯基苯乙酮 溴化反应 ω ω-二溴对苯基苯乙酮 精细化工中间体 p-phenyl acetophenone bromination ω ω-dibromo-p-phenyl acetophenone fine chemical intermediates
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参考文献15

  • 1Ajda P, Stojan S, Marko Z, et al. Free radical bromination by the H2O2-HBr system on water [ J ]. Tetrahedron Letters, 2006,47 : 7245 - 7247.
  • 2Abu T K,Tasneem P,Lokman H C,et al. A simple synthetic protocol for oxidation of alkyl-arenes into ketones using a combination of HBr - H2O2 [ J ]. Tetrahedron Letters, 2007,48 : 2271 C227.
  • 3樊能延.有机合成事典[M].北京:北京理工大学出版社,1992.332.
  • 4Kati M A, Alan Aitken R. Rearrangement during halogenation of 2- hydroxy-1, 2-diphenylpropan-1-one ( α-methylbenzoin ) [ J ]. Tetrahedron ,2008,64:5217 - 5220.
  • 5Satya P, Varinder G, Rajive G, et al. Microwave-induced selective synthesis of α-bromo and α, α-dibromoalkanones using dioxanedibromide and silica gel under solvent-free conditions [ J ]. Tetrahedron Letters ,2003,44:439 - 442.
  • 6胡华勇,乐长高.[Bmim][Br_3]与羰基化合物的选择性溴化反应研究[J].化工技术与开发,2006,35(6):5-7. 被引量:7
  • 7Samar K G,Bo W,Beom S K,et al. TMS-OTf-catalyzed α- bromination of carbonyl compounds by N-bromosuccinimide [ J ]. Tetrahedron Letters, 2006,47 : 291 - 293.
  • 8Igor P, Marko Z, Stojan S. Halogenation of ketones with N- halosuccinimides under solvent-free reaction conditions [ J ]. Tetrahedron,2008 ,64 :5191 - 5199.
  • 9Sudhir S A, Suresh B W, Ramaswamy A V. Photochemical α- bromination of ketones using N-bromosuccinimide : a simple, mild and efficient method [ J ]. Tetrahedron Letters, 2007,48 : 1411 - 1415.
  • 10Biswanath D,Katta V,Harish H,et al. Sulfonic acid functionalized silica: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide [ J ]. Journal of Molecular Catalysis, 2006,253 : 107 - 111.

二级参考文献25

  • 1胡艾希.2-芳基丙酸类消炎药不对称重排法合成[J].中国医药工业杂志,1995,26(4):180-184. 被引量:14
  • 2于佩风.α-氨基苯乙酮盐酸盐和其对位取代衍生物的合成[J].化学试剂,1986,8(5):302-302.
  • 3王金科 郭翠玲 等.雷洛昔芬[J].中国新药杂志,2000,9(2):124-124.
  • 4Burke,S. D., Danheiser,R. L. Handbook of Reagents For Organic Synthesis Oxidizing and Reducing Agents, John Wiley and Sons, Chichester, 1999.
  • 5Kimpe, N. D., Verhe, R. In The Chemistry of a-Haloketones, a- Haloaldehydes and a-Haloimines; John Wileyand Sons: Chichester, 1988.
  • 6Levene,P. A. Org. Synth. 1943,coll.Ⅱ,88.
  • 7Rappe, C. Org. Syneth. 1973,53,123.
  • 8Langley, W. D. Org. Synth. 1941, Coll. Ⅰ, 127.
  • 9Klingenberg,j. j. Org. Synth. 1963, Coll. Ⅳ, 110.
  • 10cowper,R. M. Davidson, L. H. Org. synth. 1943, Coll. Ⅱ,480.

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