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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 21
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Original Articles

Convenient Synthetic Procedures for 2-Bromofuran and 2,5-Dibromofuran

M. A. Keegstra Department of Preparative Organic Chemistry of the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
,
A. J. A. Klomp Department of Preparative Organic Chemistry of the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
&
L. Brandsma Department of Preparative Organic Chemistry of the University, Debye Institute, Padualaan 8, 3584, CH, Utrecht, The Netherlands
Pages 3371-3374 | Received 24 Sep 1990, Published online: 24 Oct 2006

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Per Lind, Marcus Carlsson, Bertil Eliasson, Eirik Glimsdal, Mikael Lindgren, Cesar Lopes, Linus Boman & Patrick Norman. (2009) A theoretical and experimental study of non-linear absorption properties of substituted 2,5-di-(phenylethynyl)thiophenes and structurally related compounds. Molecular Physics 107:7, pages 629-641.
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Articles from other publishers (42)

Yi Xie, Bin Yu, Jiajun Luo, Biaolin Yin & Huanfeng Jiang. (2020) Synthesis of [2,2’]Bifuranyl‐5,5’‐dicarboxylic Acid Esters via Reductive Homocoupling of 5‐Bromofuran ‐2‐carboxylates Using Alcohols as Reductants † . Chinese Journal of Chemistry 39:1, pages 62-68.
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Yu Xue, Zexu Xue, Wenwen Zhang, Wenna Zhang, Shuai Chen, Kaiwen Lin & Jingkun Xu. (2019) Effects on optoelectronic performances of EDOT end-capped oligomers and electrochromic polymers by varying thienothiophene cores. Journal of Electroanalytical Chemistry 834, pages 150-160.
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Vishnu Ji Ram, Arun Sethi, Mahendra Nath & Ramendra Pratap. 2019. The Chemistry of Heterocycles. The Chemistry of Heterocycles 149 478 .
Leonidas-Dimitrios Syntrivanis, Luet Lok Wong & Jeremy Robertson. (2018) Hydroxylation of Eleuthoside Synthetic Intermediates by P450 BM3 (CYP102A1) . European Journal of Organic Chemistry 2018:45, pages 6369-6378.
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Artur Lik, Sangeth Jenthra, Lars Fritze, Lars Müller, Khai‐Nghi Truong & Holger Helten. (2018) From Monodisperse Thienyl‐ and Furylborane Oligomers to Polymers: Modulating the Optical Properties through the Hetarene Ratio. Chemistry – A European Journal 24:46, pages 11961-11972.
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Shijie Zhen, Jingkun Xu, Baoyang Lu, Shimin Zhang, Li Zhao & Jie Li. (2014) Tuning the optoelectronic properties of polyfuran by design of furan-EDOT monomers and free-standing films with enhanced redox stability and electrochromic performances. Electrochimica Acta 146, pages 666-678.
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Julia Rieb, Andreas Raba, Stefan Haslinger, Manuel Kaspar, Alexander Pöthig, Mirza Cokoja, Jean-Marie Basset & Fritz E. Kühn. (2014) Synthesis, Characterization, and Reactivity of Furan- and Thiophene-Functionalized Bis(N-heterocyclic carbene) Complexes of Iron(II). Inorganic Chemistry 53:18, pages 9598-9606.
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V. A. Pal’chikov & J. Robertson. (2014) Efficient procedure for the preparation of 2-bromo-5-ethylfuran and its unexpected isomerization. Russian Journal of Organic Chemistry 50:9, pages 1369-1371.
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Adva Hayoun Barak, Graham de Ruiter, Michal Lahav, Sagar Sharma, Ori Gidron, Guennadi Evmenenko, Pulak Dutta, Michael Bendikov & Milko E. van der Boom. (2013) Coordination‐Based Molecular Assemblies of Oligofurans and Oligothiophenes. Chemistry – A European Journal 19:27, pages 8821-8831.
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Alexander Hildebrandt, Dieter Schaarschmidt, Ron Claus & Heinrich Lang. (2011) Influence of Electron Delocalization in Heterocyclic Core Systems on the Electrochemical Communication in 2,5-Di- and 2,3,4,5-Tetraferrocenyl Thiophenes, Furans, and Pyrroles. Inorganic Chemistry 50:21, pages 10623-10632.
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Pavel Arsenyan, Edgars Paegle & Sergey Belyakov. (2010) A novel method for the bromination of thiophenes. Tetrahedron Letters 51:1, pages 205-208.
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Patricia A. Peart & John D. Tovar. (2009) Expanding the Realm of Furan-Based Conducting Polymers through Conjugation with 1,6-Methano[10]annulene. Macromolecules 42:13, pages 4449-4455.
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Adam W. Franz, Larisa N. Popa, Frank Rominger & Thomas J. J. Müller. (2009) First synthesis and electronic properties of diphenothiazine dumbbells bridged by heterocycles. Org. Biomol. Chem. 7:3, pages 469-475.
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Alexander S. Dudnik, Anna W. Sromek, Marina Rubina, Joseph T. Kim, Alexander V. Kel'i & Vladimir Gevorgyan. (2008) Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles. Journal of the American Chemical Society 130:4, pages 1440-1452.
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Kevin M. Shea. 2007. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist 303 343 .
Vijay Nair, Siji Thomas, Smitha C. Mathew, N. Vidya & Nigam P. Rath. (2005) Electrophilic substitution reactions of trisheteroarylmethanes: an efficient strategy to develop novel synthons for organic synthesis. Tetrahedron 61:40, pages 9533-9540.
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Anna W. Sromek, Marina Rubina & Vladimir Gevorgyan. (2005) 1,2-Halogen Migration in Haloallenyl Ketones:  Regiodivergent Synthesis of Halofurans. Journal of the American Chemical Society 127:30, pages 10500-10501.
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Mark W. Hooper & John F. Hartwig. (2003) Understanding the Coupling of Heteroaromatic Substrates:  Synthesis, Structures, and Reductive Eliminations of Heteroarylpalladium Amido Complexes. Organometallics 22:17, pages 3394-3403.
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Chinwon Rim & David Y. Son. (2003) Hyperbranched Poly(carbosilanes) from Silyl-Substituted Furans and Thiophenes. Macromolecules 36:15, pages 5580-5584.
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Mark W. Hooper, Masaru Utsunomiya & John F. Hartwig. (2003) Scope and Mechanism of Palladium-Catalyzed Amination of Five-Membered Heterocyclic Halides. The Journal of Organic Chemistry 68:7, pages 2861-2873.
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Benjamin W Gung, Hamilton Dickson & Stephany Shockley. (2001) A concise synthesis of (+)- and (−)-adociacetylene B. Tetrahedron Letters 42:29, pages 4761-4763.
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Carole Moreau, Françoise Serein-Spirau, Michel Bordeau & Claude Biran. (2001) Electrochemical Synthesis of Functional Aryl- and Heteroarylchlorosilanes. Application to the Preparation of Donor−Acceptor or Donor−Donor Organosilicon Molecules. Organometallics 20:10, pages 1910-1917.
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Masato Koreeda & Wu Yang. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
William W. Ellis, Marion Schmitz, Atta A. Arif & Peter J. Stang. (2000) Preparation, Characterization, and X-ray Crystal Structures of Helical and Syndiotactic Zinc-Based Coordination Polymers. Inorganic Chemistry 39:12, pages 2547-2557.
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Fen‐Tair Luo & Ashok C. Bajji. (2013) Efficient Synthesis of Alkyl End‐Capped Oligoheterocycles via the Use of Palladacycle Catalyst. Journal of the Chinese Chemical Society 47:1, pages 257-261.
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. 2000. Palladium in heterocyclic chemistry - A guide for the synthetic chemist. Palladium in heterocyclic chemistry - A guide for the synthetic chemist 267 296 .
Xiao-Tao Chen, Samit K. Bhattacharya, Bishan Zhou, Clare E. Gutteridge, Thomas R. R. Pettus & Samuel J. Danishefsky. (1999) The Total Synthesis of Eleutherobin. Journal of the American Chemical Society 121:28, pages 6563-6579.
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Takahito Itoh, Masato Miyachi & Masataka Kubo. (1999) Polymerization behavior of 2,5-bis(dicyanomethylene)- 2,5-dihydrofuran. Journal of Polymer Science Part A: Polymer Chemistry 37:9, pages 1285-1292.
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Carole Moreau, Françoise Serein-Spirau, Michel Bordeau & Claude Biran. (1998) High-yield electrosynthesis of furylchlorosilanes, silyl and silanylene furans. Journal of Organometallic Chemistry 570:1, pages 147-154.
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Xiao-Tao Chen, Clare E. Gutteridge, Samit K. Bhattacharya, Bishan Zhou, Thomas R. R. Pettus, Tony Hascall & Samuel J. Danishefsky. (1998) Eine konvergente Route zur Totalsynthese der Eleutheside. Angewandte Chemie 110:1-2, pages 195-197.
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Yuichi Kobayashi, Miwa Nakano & Hiroki Okui. (1997) Chiral synthesis of (+)-aspicilin by using a furyl group as the masked γ-oxo-α,β-unsaturated carboxylic acid. Tetrahedron Letters 38:51, pages 8883-8886.
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S.C Ng, I Novak, L Wang, H.H Huang & W Huang. (1997) Synthesis and electronic structure of 1,2-heteroarylethynes: Potential monomers for low bandgap conductive polymers. Tetrahedron 53:39, pages 13339-13350.
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Uwe Geißler, Manfred L. Hallensleben & Nils Rohde. (2003) Poly{arylene‐ alt ‐[bis(1‐methylpyrrolylene)]}s, 1. Synthesis and electrochemical polymerization of terarenes . Macromolecular Chemistry and Physics 197:8, pages 2565-2576.
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J. Fr�hlich & C. Hametner. (1996) Synthesis of trisubstituted furans from 2-bromo-5-methylfuranvia halogen migrations and their selective preventionsSynthese dreifachsubstituierter Furane aus 2-Brom-5-methylfuranvia Halogenwanderung und deren selektiver Verhinderung. Monatshefte f�r Chemie Chemical Monthly 127:4, pages 435-443.
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Yuri Goldberg & Howard Alper. (1994) Electrophilic halogenation of aromatics and heteroaromatics with N-halosuccinimides in a solid/liquid system using an H+ ion exchanger or ultrasonic irradiation. Journal of Molecular Catalysis 88:3, pages 377-383.
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Marco Fossatelli, Anca C.T.H.M. van der Kerk, Sergei F. Vasilevsky & Lambert Brandsma. (1992) A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues.. Tetrahedron Letters 33:29, pages 4229-4232.
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Menno A. Keegstra, Theo H.A. Peters & Lambert Brandsma. (1992) Copper(I) halide catalysed synthesis of alkyl aryl and alkyl heteroaryl ethers. Tetrahedron 48:17, pages 3633-3652.
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M. A. KEEGSTRA, A. J. A. KLOMP & L. BRANDSMA. (2010) ChemInform Abstract: Convenient Synthetic Procedures for 2‐Bromofuran and 2,5‐Dibromofuran.. ChemInform 22:22.
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