- Synthesis process of 2-bromo-4-iodo-3-methylpyridine
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The invention provides a synthesis process of 2-bromo-4-iodo-3-methylpyridine. The process is characterized by comprising the following steps: S1, carrying out halogenation reaction on 2-bromopyridineserving as a raw material to generate 2-bromo-3-iodopyridine; and S2, carrying out a halogen dance reaction on the raw material 2-bromo-3-iodopyridine to generate 2-bromo-4-iodo-3-methylpyridine. According to the invention, cheap and easily available 2-bromopyridine is used as a raw material to synthesize the raw material 2-bromo-3-iodopyridine for the halogen dance reaction, the synthesis process is also researched and optimized, a step-by-step synthesis method is adopted and the connection sequence of functional groups is changed to break through the route, the overall yield after optimization is low, and then a one-pot synthesis method is researched according to a halogen dance reaction mechanism. The process route has the characteristics of high yield, good product quality, cheap andeasily available initial raw materials and the like.
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Paragraph 0030-0031; 0032-0033
(2021/01/24)
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- A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
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A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) (3), is prepared from glycidol in four steps in 28% overall yield. pyEDOT features an ethynyl group on its ethylenedioxy bridge, allowing further functionalization by alkyne chemistry. Its usefulness is demonstrated by a series of functionalized polythiophene derivatives that were obtained by pre- and post-electropolymerization transformations, provided by the synthetic ease of the Sonogashira coupling and click chemistry.
- Huang, Xiao,Yang, Li,Emanuelsson, Rikard,Bergquist, Jonas,Str?mme, Maria,Sj?din, Martin,Gogoll, Adolf
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supporting information
p. 2682 - 2688
(2017/01/09)
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- Deprotonative metalation of chloro- and bromopyridines using amido-based bimetallic species and regioselectivity-computed CH acidity relationships
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A series of chloro- and bromopyridines have been deprotometalated by using a range of 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal combinations. Whereas lithium-zinc and lithium-cadmium bases afforded different mono- and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium-copper combination, as demonstrated by subsequent trapping with benzoyl chlorides. The obtained selectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.
- Snegaroff, Katia,Nguyen, Tan Tai,Marquise, Nada,Halauko, Yury S.,Harford, Philip J.,Roisnel, Thierry,Matulis, Vadim E.,Ivashkevich, Oleg A.,Chevallier, Floris,Wheatley, Andrew E. H.,Gros, Philippe C.,Mongin, Florence
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experimental part
p. 13284 - 13297
(2012/02/03)
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- Alternative approaches to (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the synthesis of the 1,10-phenanthroline core
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A study on the synthesis of (Z)-1,2-bis(2-bromopyridin-3-yl)ethenes, key intermediates in the preparation of 1,10-phenanthrolines, based on selective Sonogashira and Suzuki-Miyaura cross-coupling reactions has been carried out.
- Chelucci, Giorgio,Baldino, Salvatore,Pinna, Gerard A.,Sechi, Barbara
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p. 2839 - 2843
(2008/09/20)
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- Tris(2,2′-bipyridyl)ruthenium(II) with branched polyphenylene shells: A family of charged shape-persistent nanoparticles
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(Figure Presented) Cores for thought: Dendrimers based on an octahedral symmetry and with a central positively charged transition-metal complex have been prepared up to the third generation (see schematic representation). The shape-persistent dendrimers with a high density of aromatic rings are accessible by either a partly convergent synthesis or a divergent strategy in which the metal complex proved to be stable to high-temperature Diels-Alder reactions.
- Haberecht, Monika C.,Schnorr, Jan M.,Andreitchenko, Ekaterina V.,Clark Jr., Christopher G.,Wagner, Manfred,Muellen, Klaus
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scheme or table
p. 1662 - 1667
(2009/02/06)
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- A concise synthesis of 2,4-disubstituted pyridines: A convenient synthesis of 2-bromo-4-iodopyridine via halogen dance and its successive one-pot disubstitutions
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As a key building block for 2,4-disubstituted pyridines, 2-bromo-4-iodopyridine was synthesized conveniently from 2-bromopyridine using LDA and I2 via 'halogen dance'. 2-Bromo-4-iodopyridine was then converted to other 2,4-diaryl pyridines and
- Duan, Xin-Fang,Li, Xiang-Hong,Li, Fu-You,Huang, Chun-Hui
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p. 2614 - 2616
(2007/10/03)
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- Coupling reaction of zirconacyclopentadienes with dihalonaphthalenes and dihalopyridines: A new procedure for the preparation of substituted anthracenes, quinolines, and isoquinolines
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Reactions of tetraiodobenzene with zirconacyclopentadienes, which were conveniently prepared from two alkynes (or diynes) and zirconocene complexes, afforded 1,2,3,4-tetrasubstituted diiodonaphthalene derivatives in good isolated yields. These 1,2,3,4-tetrasubstituted diiodonaphthalene derivatives could be converted to 1,2,3,4,5,6,7,8-octasubstituted anthracene derivatives by reaction with a second zirconacyclopentadiene. When the two zirconacyclopentadienes were different, unsymmetrical anthracenes such as 1,2,3,4-tetraethyl-5,6,7,8-tetraphenylanthracene (68% isolated yield) were obtained. On the other hand, treatment of a 2,3-dihalopyridine such as 2-bromo-3-iodopyridine with zirconacyclopentadienes gave 5,6,7,8-tetrasubstituted quinoline derivatives in good to high yields. 3,4-Dihalopyridines such as 4-chloro-3-iodopyridine reacted with zirconacyclopentadienes to afford 5,6,7,8-tetrasubstituted isoquinoline derivatives in good to high yields.
- Takahashi, Tamotsu,Li, Yanzhong,Stepnicka, Petr,Kitamura, Masanori,Liu, Yanjun,Nakajima, Kiyohiko,Kotora, Martin
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p. 576 - 582
(2007/10/03)
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- Regiocontrolled deprotonative-zincation of bromopyridines using aminozincates
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Regiochemistry in the deprotonation of bromopyridines was found to be greatly influenced by the choice of metal amide base, and DA-zincate and TMP-zincate turned out to be excellent complementary practical agents for regioselective metalation of bromopyri
- Imahori,Uchiyama,Sakamoto,Kondo
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p. 2450 - 2451
(2007/10/03)
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- New syntheses of substituted pyridines via bromine-magnesium exchange
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Bromine-magnesium exchange using iPrMgCl in THF at room temperature on 2-, 3- and 4-bromopyridines allowed the synthesis of various functionalized pyridines. The methodology was successfully used for the synthesis of 4- azaxanthone. Moreover, single exchange reactions observed on 2,6-, 3,5-, 2,3- and 2,5-dibromopyridines, with complete regioselectivity in the case of 2,3- and 2,5-dibromopyridines, afforded substituted bromopyridines, which were then involved in a second exchange step to provide difunctionalized pyridines. (C) 2000 Elsevier Science Ltd.
- Trécourt, Fran?ois,Breton, Gilles,Bonnet, Véronique,Mongin, Florence,Marsais, Francis,Quéguiner, Guy
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p. 1349 - 1360
(2007/10/03)
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