Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 6
683
Views
20
CrossRef citations to date
0
Altmetric
Original Articles

Efficient and Regioselective Bromination of Aromatic Compounds with Ethylenebis(N-methylimidazolium) Ditribromide (EBMIDTB)

, , &
Pages 868-876 | Received 17 Mar 2009, Published online: 22 Feb 2010

REFERENCES

  • (a) Christophersen , C. Secondary metabolites from marine bryozoans—A review . Acta Chem. Scand. 1985 , 39B , 517 – 529 ; (b) Muathen , H. A. 1,8-Diazabicyclo[5.4.0] undec-7-ene hydrobromide perbromide: A new mild stable brominating agent for aromatic compounds . J. Org. Chem. 1992 , 57 , 2740 – 2741 ; (c) Butler , A. ; Walker , J. V. Marine haloperoxidases . Chem. Rev. 1993 , 93 , 1937 – 1944 ; (d) Katritzky , A. R. ; Li , J. Q. ; Stevens , C. V. ; Ager , D. J. An alternative synthesis of aryl and heteroaryl bromides from activated aryl hydroxy compounds . Org. Prep. Proced. Int. 1994 , 26 , 439 – 444 ; (e) Ullmann's Encyclopedia of Industrial Chemistry, 6th ed.; Wiley-VCH: Weinheim, 1998 .
  • Stille , J. K. Palladium catalyzed coupling of organotin reagents with organic electrophiles. Pure Appl. Chem. 1985, 57, 1771–1780.
  • (a) Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds . Chem. Rev. 1995 , 95 , 2457 – 2483 ; (b) Herrmann , W. A. ; Reisinger , C. P. ; Haerter , P. In Aqueous-Phase Organometallic Catalysis; B. Cornils, Herrmann, W. A. (Eds.); Wiley-VCH: Weinheim, Germany, 2004; pp. 511–523 ; (c) Zhao , D. B. ; Fei , Z. F. ; Geldbach , T. J. ; Scopelliti , R. ; Dyson , P. J. Nitrile-functionalized pyridinium ionic liquids: Synthesis, characterization, and their application in carbon–carbon coupling reactions . J. Am. Chem. Soc. 2004 , 126 , 15876 – 15882 ; (d) Spivey , A. C. ; Gripton , C. J. G. ; Hannah , J. P. Recent advances in group 14 cross-coupling: Si and Ge-based alternatives to the Stille reaction . Curr. Org. Synth. 2004 , 1 , 211 – 226 ; (e) Bedford , R. B. ; Hazlewood , S. L. ; Limmert , M. E. ; Albisson , D. A. ; Draper , S. M. ; Scully , P. N. ; Coles , S. J. ; Hursthouse , M. B. Ortho-palladated and platinated bulky triarylphosphite complexes: Synthesis, reactivity, and application as high-activity catalysts for Suzuki and Stille coupling reactions . Chem. Eur. J. 2003 , 9 , 3216 – 3227 ; (f) Choudary , B. M. ; Madhi , S. ; Chowdari , N. S. ; Kantam , M. L. ; Sreedhar , B. Layered double-hydroxide-supported nanopalladium catalyst for Heck, Suzuki, Sonogashira, and Stille-type coupling reactions of chloroarenes . J. Am. Chem. Soc. 2002 , 124 , 14127 – 14136 .
  • (a) Beletskaya , I. P. ; Cheprakov , A. V. The Heck reaction as a sharpening stone of palladium catalysis . Chem. Rev. 2000 , 100 , 3009 – 3066 ; (b) Eberhard , M. R. Insights into the Heck reaction with PCP pincer palladium(II) complexes . Org. Lett. 2004 , 6 , 2125 – 2128 ; (c) Oestreich , M. ; Sempere-Culler , F. ; Machotta , A. B. Catalytic desymmetrizing intramolecular Heck reaction: Evidence for an unusual hydroxy-directed migratory insertion . Angew. Chem. Int. Ed. 2005 , 44 , 149 – 152 ; (d) Kressierer , C. J. ; Muller , T. J. J. Novel three-component reactions based on a Heck carbopalladation/cyclization domino reaction . Angew. Chem. Int. Ed. 2004 , 43 , 5997 – 6000 ; (e) Braese , S. ; de Meijere , A. Metal-Catalyzed Cross-Coupling Reactions; A. De Meijere, F. Diederich (Eds.); Wiley-VCH: Weinheim, Germany, 2004; pp. 217–315 .
  • (a) Sonogashira , K. Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon Press : New York , 1991 ; vol. 3 , p. 521 ; (b) García , D. ; Cuadro , A. M. ; Alvarez-Builla , J. ; Vaquero , J. J. Sonogashira reaction on quinolizium cations. Org. Lett. 2004, 6, 4175–4178 ; (c) Urgaonkar , S. ; Verkade , J. G. Ligand-, copper-, and amine-free Sonogashira reaction of aryl iodides and bromides with terminal alkynes. J. Org. Chem. 2004, 69, 5752–5755 .
  • (a) Hartwig , J. F. Transition-metal-catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism . Angew. Chem. Int. Ed. 1998 , 37 , 2047 – 2067 ; (b) Wolfe , J. P. ; Wagaw , S. ; Marcoux , J. F. ; Buchwald , S. L. Rational development of practical catalysts for aromatic carbon–nitrogen bond formation . Acc. Chem. Res. 1998 , 31 , 805 – 818 .
  • Bora , U. ; Bose , G. ; Chaudhuri , M. K. ; Dhar , S. S. ; Gopinath , R. ; Khan , A. T. ; Patel , B. K. Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2: An environmentally favorable synthetic protocol . Org. Lett. 2000 , 2 , 247 – 249 .
  • Schmid , H. Bromierungen mit brom-succinimid bei gegenwart von katalysatoren, II . Helv. Chim. Acta 1946 , 29 , 1144 – 1151 .
  • Duan , J. X. ; Zhang , L. H. ; Dolbier , W. R. A convenient new method for the bromination of deactivated aromatic compounds . Synlett 1999 , 1245 – 1246 .
  • Auerbach , J. ; Weissman , S. A. ; Blacklock , T. J. ; Angeles , M. R. ; Hoogsteen , K. N-Bromosuccinimide/dibromodimethylhydantoin in aqueous base: A practical method for the bromination of activated benzoic acids . Tetrahedron Lett. 1993 , 34 , 931 – 934 .
  • Konishi , H. ; Aritomi , K. ; Okano , T. ; Kiji , J. A mild selective monobromination reagent system for alkoxybenzenes: N-Bromosuccinimide–silica gel. Bull. Chem. Soc. Jpn. 1989, 62, 591–593.
  • Ranu , B. C. ; Sarkar , D. C. ; Chakraborty , R. A simple and improved procedure for selective ring bromination of alkyl-substituted aromatic-hydrocarbons on the surface of alumina . Synth. Commun. 1992 , 22 , 1095 – 1099 .
  • Goldberg , Y. ; Alper , H. Electrophilic halogenation of aromatics and heteroaromatics with N-halosuccinimides in a solid/liquid system using an H+ ion exchanger or ultrasonic irradiation . J. Mol. Catal. 1994 , 88 , 377 – 383 .
  • Paul , V. ; Sudalai , A. ; Daniel , T. ; Srinivasan , K. V. Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5 . Tetrahedron Lett. 1994 , 35 , 7055 – 7056 .
  • Barhate , N. B. ; Gajare , A. S. ; Wakharkar , R. D. ; Bedekar , A. V. Simple and efficient chlorination and bromination of aromatic compounds with aqueous TBHP (or H2O2) and a hydrohalic acid . Tetrahedron Lett. 1998 , 39 , 6349 – 6350 .
  • Das , B. ; Venkateswarlu , K. ; Krishnaiah , M. ; Holla , H. An efficient, rapid, and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst . Tetrahedron Lett. 2006 , 47 , 8693 – 8697 .
  • Prakash , G. K. S. ; Mathew , T. ; Hoole , D. ; Esteves , P. M. ; Wang , Q. ; Rasul , G. ; Olah , G. A. N-Halosuccinimide/BF3-H2O: Efficient electrophilic halogenating systems for aromatics . J. Am. Chem. Soc. 2004 , 126 , 15770 – 15776 .
  • Das , B. ; Venkateswarlu , K. ; Majhi , A. ; Siddaiah , V. ; Reddy , K. R. A facile nuclear bromination of phenols and anilines using NBS in the presence of ammonium acetate as a catalyst . J. Mol. Catal. A: Chem. 2007 , 267 , 30 – 33 .
  • Ganguly , N. C. ; De , P. ; Dutta , S. Mild regioselective monobromination of activated aromatics and hetero-aromatics with N-bromosuccinimide in tetrabutylammonium bromide . Synthesis 2005 , 1103 – 1108 .
  • (a) Kalyani , D. ; Dick , A. R. ; Anani , W. Q. ; Sanford , M. S. A simple catalytic method for the regioselective halogenation of arenes . Org. Lett. 2006 , 8 , 2523 – 2526 ; (b) Kalyani , D. ; Dick , A. R. ; Anani , W. Q. ; Sanford , M. S. Scope and selectivity in palladium-catalyzed directed C-H bond halogenation reactions . Tetrahedron 2006 , 62 , 11483 – 11498 .
  • Pravst , I. ; Zupan , M. ; Stavber , S. Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions . Tetrahedron 2008 , 64 , 5191 – 5199 .
  • Heravi , M. M. ; Abdolhosseini , N. ; Oskooie , H. A. Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine . Tetrahedron Lett. 2005 , 46 , 8959 – 8963 .
  • Gnaim , J. M. ; Sheldon , R. A. Regioselective bromination of aromatic compounds with Br2/SO2Cl2 over microporous catalysts . Tetrahedron Lett. 2005 , 46 , 4465 – 4468 .
  • De Almeida , L. S. ; Esteves , P. M. ; De Mattos , M. C. S. A new regioselective bromination of activated aromatic rings . Synthesis 2006 , 221 – 223 .
  • De Almeida , L. S. ; Esteves , P. M. ; De Mattos , M. C. S. Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions . Synlett 2007 , 1687 – 1690 .
  • Moriuchi , T. ; Yamaguchi , M. ; Kikushima , K. ; Hirao , T. An efficient vanadium-catalyzed bromination reaction . Tetrahedron Lett. 2007 , 48 , 2667 – 2670 .
  • Karade , N. N. ; Tiwari , G. B. ; Huple , D. B. ; Siddiqui , T. A. J. Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr, or I2 . J. Chem. Res. Synop. 2006 , 366 – 368 .
  • Bhatt , S. ; Nayak , S. K. Copper(II) bromide: A simple and selective monobromination reagent for electron-rich aromatic compounds . Synth. Commun. 2007 , 37 , 1381 – 1388 .
  • Fieser , L. F. ; Fieser , M. Reagents for Organic Synthesis ; Wiley : New York , 1967; pp. 967.
  • Cattaway , F. D. ; Hoyle , G. Perhalides of quaternary ammonium salts . J. Chem. Soc. 1923 , 654 – 662 .
  • Avramoff , M. ; Weiss , J. ; Schaechter , O. The brominating properties of tetramethylammonium tribromide . J. Org. Chem. 1963 , 28 , 3256 – 3258 .
  • Kajianeshi , S. ; Kakinami , T. ; Tokiyama , H. ; Hirakawa , T. ; Okamoto , T. Bromination of phenols by use of benzyltrimethylammonium tribromide . Chem. Lett. 1987 , 627 – 630 .
  • Kar , G. ; Saikia , A. K. ; Bora , U. ; Dehury , S. K. ; Chaudhuri , M. K. Synthesis of cetyltrimethylammonium tribromide (CTMATB) and its application in the selective oxidation of sulfides to sulfoxides . Tetrahedron Lett. 2003 , 44 , 4503 – 4505 .
  • Buckles , R. E. ; Popov , A. I. ; Zelezny , W. F. ; Smith , R. J. Spectrophotometric study of tetrabutylammonium tribromide . J. Am. Chem. Soc. 1951 , 73 , 4525 – 4528 .
  • Kavala , V. ; Naik , S. ; Patel , B. K. A new recyclable ditribromide reagent for efficient bromination under solvent-free condition . J. Org. Chem. 2005 , 70 , 4267 – 4271 .
  • (a) Cerichelli , G. ; Luchetti , L. ; Mancini , G. Surfactant control of the ortho/para ratio in the bromination of anilines, 4 . Colloids Surf. A. 2006 , 289 , 226 – 228 ; (b) Salazar , J. ; Dorta , R. Pentylpyridinium tribromide: A vapor pressure free room temperature ionic liquid analogue of bromine . Synlett 2004 , 1318 – 1320 .
  • (a) Le , Z. G. ; Chen , Z. C. ; Hu , Y. ; Zheng , Q. G. as a new reagent for regioselective mono-bromination of activated aromatics under solvent-free conditions . Chin. Chem. Lett. 2005 , 16 , 1007 – 1009 ; (b) Le , Z. G. ; Chen , Z. C. ; Hu , Y. ; Zheng , Q. G. [Bmim]Br(3) as a new reagent for regioselective monobromination of arylamines under solvent-free conditions . Synthesis 2004 , 2809 – 2812 .
  • (a) Pravst , I. ; Zupan , M. ; Stavber , S. Intoduction of halogen atoms into organic compounds under solvent-free reaction conditions . Curr. Org. Chem. 2009 , 13 , 47 – 70 ; (b) Chiappe , C. ; Leandri , E. ; Pieraccini , D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent . Chem. Commun. 2004 , 22 , 2536 – 2537 ; (c) Toda , F. ; Schmeyers , J. Selective solid-state brominations of anilines and phenols . Green Chem. 2003 , 5 , 701 – 703 .
  • Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Lasemi , Z. Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters . Monatsh. Chem. 2009 , 140 , 57 – 60 .
  • (a) Buckingham , J. ; Donaghy , S. M. Dictionary of Organic Compounds, , 6th ed. ; Chapman and Hall : London , 1982 ; (b) Kaiser , F. ; Schwink , L. ; Velder , J. ; Schmalz , H. G. Studies towards the total synthesis of mumbaistatin: Synthesis of highly substituted benzophenone and anthraquinone building blocks. Tetrahedron 2003, 59, 3201–3217 ; (c) Chrtien , J. M. ; Zammattio , F. ; Le Grognec , E. ; Paris , M. ; Cahingt , B. ; Montavon , G. ; Quintard , J. P. Polymer-supported organotin reagents for regioselective halogenation of aromatic amines. J. Org. Chem. 2005, 70, 2870–2873 ; (d) http://www.chemexper.com/search/cas/39263326.html ; (e) Kochergin , P. M. Imidazole series, XV: Reaction products of N,N′-dimethyl oxamide with pentahalo phosphorus compounds. Zh. Obshch. Khim. 1964, 34, 3402–3407 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.