Tag: M.W=200-300

Electric Literature of 883502-14-5, A common heterocyclic compound, 883502-14-5, name is 1-Fluoro-2-iodo-3-methylbenzene, molecular formula is C7H6FI, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step A: 2-Fluoro-6-methyl-benzonitrile: A 10 L round bottom flask equipped with adapter,thermocouple and stir bar was charged with DMA (6 L) and degassed under vacuum and purgedwith N2 three times. To the mixture was added Palladium Tetrakis triphenylphosphine (87.5 g,72.0 mmol) and the mixture was degassed under vacuum and purged with N2 three times. Thereaction was heated to 80 C for 30 min. 3-Fluoro-2-iodotoluene (575 g, 2.4 mol) and ZincCyanide (I7I.7 g, 1.46 mol) were added and the mixture was degassed under vacuum and purgedwith N2 three times. The reaction mixture was heated to 80 C for 16 h and then allowed to cooltoRT. The solution was added to a 2.0 L aqueous solution of IN NH40H and extracted three times with 1.5 L EtOAc. The extracts were washed with 2 L brine, dried over Na2S04, filteredand concentrated. The crude product was treated with mCPBA in cooled DCM and then purifiedby chromatography (PE/EA = IO:I) to get the title compound.

The synthetic route of 883502-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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Synthetic Route of 41252-96-4, A common heterocyclic compound, 41252-96-4, name is 2-Chloro-1-iodo-4-nitrobenzene, molecular formula is C6H3ClINO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of the aryl iodide (1.0 mmol), 10% Pd/C (0.05 mmol), PPh3 (0.20 mmol), and K2CO3 (2.0 mmol) was stirred in H2O (5 mL) at room temperature under an argon atmosphere. 2-Imino-1-(2-propynyl)pyrimidine (2) (1.20 mmol) was added, and the mixture was stirred at 95 C for 10 h. After completion of the reaction, the resulting solution was concentrated in vacuo, and the crude product was subjected to column chromatography (silica gel) using CHCl3-CH3OH (98:2) as eluent to afford the pure product.

The synthetic route of 41252-96-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bakherad, Mohammad; Keivanloo, Ali; Kalantar, Zahra; Jajarmi, Saeideh; Tetrahedron Letters; vol. 52; 2; (2011); p. 228 – 230;,
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Synthetic Route of 13421-13-1,Some common heterocyclic compound, 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 21 To a solution of 1.28 g. (0.01 mol) of p-fluorothiophenol and 2.82 g. (0.01 mol) of 2-iodo-4-chlorobenzoic acid in 20 ml. of pyridine is added 1.3 g. (0.01 mol) of potassium carbonate, with stirring. Additional pyridine is added until solution is clear and then 0.3 g. of cuprous chloride is introduced. The resulting mixture is refluxed overnight, poured into ice-water, stirred and filtered. The aqueous solution is acidified and filtered. The solid is dissolved in 5% sodium bicarbonate solution and this solution is extracted with ether. The aqueous solution is acidified, extracted with ether and the washed, dried extract is concentrated to give 4-chloro-2-(4-fluorophenylthio)-benzoic acid, m.p. 204-213 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; SmithKline Corporation; US4086350; (1978); A;,
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Related Products of 696-41-3,Some common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, molecular formula is C7H5IO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 136 tert-butyl ({4-(2-fluorophenyl)-5-[(3-formylphenyl)thio]-1,3-thiazol-2-yl}methyl)methylcarbamate To a solution of 2-ethylhexyl 3-{[2-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-4-(2-fluorophenyl)-1,3-thiazol-5-yl]thio}propanoate (749 mg) in ethanol (10 mL) was added sodium ethoxide (381 mg) at 0 C., and the mixture was stirred at room temperature for 4 hr, and concentrated under reduced pressure. A mixture of the residue, 3-iodobenzaldehyde (489 mg), tris(dibenzylideneacetone)dipalladium(0) (35 mg) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthine (81 mg) in toluene (10 mL) was stirred at 80 C. for 3 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a yellow oil (676 mg, yield quantitative). 1H-NMR (CDCl3) delta: 1.47 (9H, brs), 3.00 (3H, brs), 4.69 (2H, brs), 7.10-7.20 (3H, m), 7.34-7.50 (3H, m), 7.65-7.68 (2H, m), 9.90 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodobenzaldehyde, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/156642; (2009); A1;,
Iodide – Wikipedia,
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Related Products of 1437316-91-0, A common heterocyclic compound, 1437316-91-0, name is 2,4-Difluoro-3-iodoaniline, molecular formula is C6H4F2IN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2,4-difluoro-3-iodoaniline (255 mg, 1 mmol) in 1,2_dichloroethane (3 mL) was slowly added dropwise a solution of P to pyridine (lmL), propylsulfonyl chloride (157 mg, 1. lmmol). The reaction solution was heated under reflux for 2 hours, cooled and concentrated in vacuo to remove the solvent. The resulting oil was dissolved in ethyl acetate (20 mL) and washed with 5% sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give N- (2,4-difluoro-3- Iodophenyl) propane-1-sulfonamide (298 mg, 83%).

The synthetic route of 1437316-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Xiao Dengming; Li Jijun; Zhu Yan; Hu Yuandong; Wang Huting; Wang Zhe; Wang Zanping; Wei Yongheng; Sun Yinghui; Wu Qiong; Zhang Hui; Peng Yong; Kong Fansheng; Sun Ying; Luo Hong; Han Yongxin; (64 pag.)CN103102349; (2017); B;,
Iodide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 41252-96-4, name is 2-Chloro-1-iodo-4-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-1-iodo-4-nitrobenzene

General procedure: 4-acryloyloxy-2,2,6,6-tetramethylpiperidin-1-oxyl (3, 0.113 g,0.5 mmol), aryl iodide (4a-i, 0.5 mmol), Bu4N+AcO- (hygroscopic)(0.3 g), PdEnCatTOTP30 (0.0625 g, 0.025 mol,5 mol %), and toluene (2 mL) were placed in a flask, stirred and heated at 80-100 C for 20-27 h under argon. The particular temperatures and times of the reactions are summarized in Table 1. After approximately 6 h, a second portion of a catalyst(0.0625 g, 0.025 mol, 5 mol %) was added. The progress of the reaction was monitored by TLC (silica, hexane/ethyl acetate9:1). Upon completion of the reaction, the solids were filtered off, the dark filtrate was concentrated under reduced pressureand subjected to column chromatography (hexane/ethyl acetate 9:1, benzene/ethyl acetate 95:5, benzene/methanol 95:5 aspossible mobile phases). The red zone was collected, the eluate was evaporated under reduced pressure to yield red oils (solidifiedin a refrigerator), or directly red crystals of 5a-i.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 41252-96-4.

Reference:
Article; Zakrzewski, Jerzy; Huras, Bogumila; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1155 – 1162;,
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2401-21-0, name is 1,2-Dichloro-3-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1,2-Dichloro-3-iodobenzene

G. 17alpha-Chloro-17beta-(3′,4′-Dichlorobenzylsulfinyl)-1,4-Androstadiene-3,11-Dione In a manner similar to that described in Example 2A, react 0.238 gms. of 17alpha-(3′,4′-dichlorobenzylthio)-1,4-androstadiene-3,11-dione, 8 ml. of pyridine, 2 ml. of water and 0.411 gm. of iodobenzene dichloride. Purify the residue utilizing thin layer silica gel chromatography, developing with ethyl acetate/chloroform (1:4) and eluding with ethyl acetate. Crystallize the major band from ether to obtain the title compound; m.p.=249¡ã-251¡ã C.

The synthetic route of 2401-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US4183924; (1980); A;,
Iodide – Wikipedia,
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Electric Literature of 31599-61-8,Some common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, molecular formula is C8H9I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

The synthetic route of 31599-61-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bisht, Narendra; Babu, Srinivasarao Arulananda; Tetrahedron; vol. 72; 39; (2016); p. 5886 – 5897;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H4ClFIN

General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

The synthetic route of 216393-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Sai-Lan; Qiu, Li-Hua; Sun, Ru; Yang, Ling; Ge, Jian-Feng; Dyes and Pigments; vol. 160; (2019); p. 58 – 63;,
Iodide – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9IO2

General procedure: A mixture of the styrene (3 mmol), the halogenated benzene (3 mmol), triethanolamine (3 mmol) and Pd (II) acetate (0.03 g) was stirred under argon at 100 C for 24 h. The reaction was cooled to 25 C, quenched by the addition of dil. aq. hydrochloric acid (2 N, 10 ml), and extracted with ether (3 ¡Á 100 ml). The organic phases were dried (Na2SO4), the solvents evaporated, and the crude product was subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Csuk, Rene; Albert, Sabrina; Siewert, Bianka; Schwarz, Stefan; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 669 – 678;,
Iodide – Wikipedia,
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