Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/49427

TitleReactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling
Author(s)Raposo, M. Manuela M.
Costa, Susana P. G.
Batista, Rosa Maria Ferreira
Ferreira, Rosa Cristina Moutinho
KeywordsChromatography
NMR
Suzuki-Miyaura cross-coupling
Thiophene
Boronic acid
Aldehyde
Synthesis
Reactivity studies
Organic Chemistry Experiments
Laboratory Classroom
Issue date2016
PublisherRoyal Society of Chemistry
CitationRaposo, M. M. M.; Costa, S. P. G.: Batista, R. M. F.; Ferreira, R. C. M. in Comprehensive Organic Chemistry Experiments for the Laboratory Classroom (COCELC), “Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling”, Afonso, C. A. M.; Franzén, R.; Tan, B.; Candeias, N. R.; Simão, D.; Trindade, A.; Coelho, J. (Eds); Royal Society of Chemistry 2016, Chapter 142, Experiment 7.2., p 628-632 (ISBN 978-18-49739-63-4).
Abstract(s)The aim of this work is the synthesis of a formyl-arylthiophene derivative, using simple experimental techniques and commercially available reagents. The synthesis of this compound involves a palladium catalysed cross-coupling reaction (Suzuki-Miyaura coupling), between a boronic acid derivative and a heterocyclic brominated compound using DME as solvent and Na2CO3 as base. Different coupling components would be used in order to determine the influence of the structure of the boronic acid as well as the brominated compound on the yield of the Suzuki-Miyaura coupling reaction. Several experimental techniques will be considered such as heating at reflux under an inert atmosphere, liquid-liquid extraction, gravity and vacuum filtration, thin layer chromatography (TLC), column chromatography on silica gel and melting point. The determination of the structure of the compound synthesized will be also performed through 1H NMR and IR spectroscopic techniques. The duration of the experiment will be 3 sessions: session 1: preparation of 5-phenylthiophene-2-carbaldehyde; session 2: isolation of 5-phenylthiophene-2-carbaldehyde; session 3: purification of 5-phenylthiophene-2-carbaldehyde using column chromatography on silica gel. The difficulty level of this experiment is medium and the level of study is intermediate.
TypeBook part
DescriptionEste capítulo de livro constitui uma experiência que pode ser usada como parte da componente prática de uma unidade curricular de química orgânica.
URIhttp://hdl.handle.net/1822/49427
ISBN978-18-49739-63-4
Publisher versionhttp://pubs.rsc.org/en/content/ebook/978-1-84973-963-4#!divbookcontent
AccessRestricted access (Author)
Appears in Collections:CDQuim - Livros e Capítulos de Livros / Books and Book Chapters

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