3,4,5-三氟-2'-硝基联苯的工艺合成

doi:10.16085/j.issn.1000-6613.2015.04.038

化工进展 ›› 2015, Vol. 34 ›› Issue (04): 1122-1125.DOI: 10.16085/j.issn.1000-6613.2015.04.038

3,4,5-三氟-2'-硝基联苯的工艺合成

刘承先

常州工程职业技术学院, 江苏常州 213164

收稿日期:2014-12-16 修回日期:2015-01-04 出版日期:2015-04-05 发布日期:2015-04-05
作者简介:刘承先,(1963—),男,副教授,主要研究方向为化学工程与工艺.E-mail cxliu@email.czie.net.

Synthesis of 3,4,5-trifluoro-2'-nitro-1,1'-biphenyl

LIU Chengxian

Deparmtment of Chemical Engineering, Changzhou Institute of Engineering Technology, Changzhou 213164, Jiangsu, China

Received:2014-12-16 Revised:2015-01-04 Online:2015-04-05 Published:2015-04-05

摘要/Abstract

摘要： 3,4,5-三氟-2'-硝基联苯是合成杀菌剂氟唑菌酰胺的重要原料.本文考察了以3,4,5-三氟苯硼酸与邻氯硝基苯为原料,Ms-Pd(分子筛负载氯化钯)作为偶联反应催化剂,制备3,4,5-三氟-2'-硝基联苯.通过反应条件优化,实验确定的最佳反应条件是:以Ms-Pd为催化剂,碳酸钾为缚酸剂, DMF为反应溶剂,邻氯硝基苯和3,4,5-三氟苯硼酸进行反应,反应温度40℃,反应时间10h.产品收率92%,液相含量98.3%.催化剂Ms-Pd套用4次活性无降低.

关键词: 3,4,5-三氟-2'-硝基联苯, 偶联反应, Ms-Pd

Abstract: 3,4,5-trifluoro-2'-nitro-1,1-biphenyl was an important intermediate for the synthesis of Fluxapyroxad. It was obtained with 3,4,5-trifluorophenyl boronic acid and 1-chloro-2-nitrobenzene as starting materials,Ms-Pd as the catalyst of coupling reaction. The optimal reaction condition was obtained as reaction temperature of 40℃,and reaction time of 10h,with Ms-Pd as catalyst,DMF as solvent,K₂CO₃ as deacid reagen,1-chloro-2-nitrobenzene and 3,4,5-trifluorophenyl boronic acid as reactants. Under the optimal condition,a yield of 92% was obtained. The product content was 98.3%. Ms-Pd catalyst activity remained after four time recycling.

Key words: 3,4,5-trifluoro-2'-nitro-1,1'-biphenyl, coupling reaction, Ms-Pd

中图分类号:

TQ246.1⁺3

刘承先. 3,4,5-三氟-2'-硝基联苯的工艺合成[J]. 化工进展, 2015, 34(04): 1122-1125.

LIU Chengxian. Synthesis of 3,4,5-trifluoro-2'-nitro-1,1'-biphenyl[J]. Chemical Industry and Engineering Progree, 2015, 34(04): 1122-1125.

参考文献

[1] Jasch H,Scheumann J,Heinrich M R. Regioselective radical arylation of anilines with arylhydrazines[J]. J. Org. Chem.,2012,77(23):10699- 10706.
[2] Wolfgang R,Christopher K,Peer S S,et al. Method for manufacturing aryl carboxamides:WO,2009135860[P]. 2009-11-12.
[3] Volker M,Peer S S,Kathrin W S,et al. Method for producing substituted biphenyls:WO,2009156359[P]. 2009-12-30.
[4] Shabalin A Y,Adonin N Y,Bardin V V,et al. The influence of the nature of phosphine ligand on palladium catalysts for cross-coupling of weakly nucleophilic potassium pentafluorophenyltrifluoroborate with ArHal and PhCH₂Hal (Hal=Br,Cl)[J]. Tetrahedron,2014,70 (10):3720- 3725.
[5] Zhao Huaiqing,Wei Ye ,Xu Jing,et al. Pd/PR₃-catalyzed cross-coupling of aromatic carboxylic acids with electron-deficient polyfluoroarenes via combination of decarboxylation with sp2 C-H cleavage[J]. J. Org. Chem.,2011,76(3):882-893.
[6] Xie Kai,Yang Zhiyong,Zhou Xingjian,et al. Pd-catalyzed decarboxylative arylation of thiazole,benzoxazole,and polyfluorobenzene with substituted benzoic acids[J]. Org. Lett.,2010,12(7):1564-1567.
[7] Yin Liang,Zhang Zhanhui,Wang Yongmei. PEG (300)-PdCl₂ promoted efficient and convenient Suzuki-Miyaura coupling of aryl chlorides with arylboronic acids[J] . Tetrahedron,2006,62(40):9359-9364.
[8] Korte A,Lohmann J K.,Grote T,et al. Process for the preparation of substituted 2-nitrobiphenyls:WO,2010102980[P]. 2010-09-16.
[9] Nicolay Y. AdoninD,Babushkin E.,et al. The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C₆F₅BF₃] with aryl iodides and aryl bromides[J]. Tetrahedron,2008,64(25):5920-5924.
[10] Dey R,Sreedhar B,Ranu B C. Molecular sieves supported palladium(Ⅱ) catalyst:Suzuki coupling of chloroarenes and an easy access to useful intermediates for the synthesis of irbesartan,losartan and boscalid[J]. Tetrahedron,2010,66(13):2301–2305.

3,4,5-三氟-2'-硝基联苯的工艺合成

Synthesis of 3,4,5-trifluoro-2'-nitro-1,1'-biphenyl

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 5

编辑推荐

Metrics

本文评价

[1]	李庆林, 宋涛, 杨勇. 生物质炭基材料在有机催化转化中的应用[J]. 化工进展, 2021, 40(4): 1966-1982.
[2]	周人杰, 陈瑜, 张玉飞, 安静雯, 姜珊, 黄璐, 李鹤. 二茂铁硼酸在合成反应中的研究进展[J]. 化工进展, 2017, 36(S1): 388-393.
[3]	阚文涛，胡睿，钟正坤. Sonogashira偶联反应的过渡金属催化剂研究进展[J]. 化工进展, 2013, 32(04): 804-808.
[4]	张文雯1，罗放2，陈绘如1，王炳恒1，吉民2. 左旋甲状腺素钠合成工艺的改进[J]. 化工进展, 2011, 30(12): 2743-.
[5]	陈田，杨运泉，刘文英，王威燕，周国平. 6-(4-苯磺酰基-3-甲基-2-丁烯)-基-2,3-二甲氧基-5-甲基氢醌双苄醚的合成 [J]. 化工进展, 2008, 27(5): 745-.