Category: iodides-buliding-blocks

103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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. category: iodides-buliding-blocks

Example 8 Preparation of 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C5) (0174) (0175) 3-(4-Bromophenyl)-1H-1,2,4-triazole (C4) (10.9 g, 48.5 mmol), copper(I) iodide (2.38 g, 12.5 mmol), and cesium carbonate (30.3 g, 93.0 mmol) in a round-bottomed flask was flushed with nitrogen. Dimethylsulfoxide (85 mL) was added, followed by 1-iodo-4-(trifluoromethoxy)benzene (13.2 g, 45.8 mmol). The reaction was degassed for 5 minutes, then heated at 100¡ã C. for 3 days. The reaction was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of Celite? rinsing with ethyl acetate. To the filtrate was added saturated ammonium chloride and stirred for 1.5 hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3¡Á). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite?. Purification by flash column chromatography using 0-40percent EtOAc/hexanes as eluent provided the title compound as an off-white solid (9.65 g, 52percent): mp 109-112¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H), 8.10-8.03 (m, 2H), 7.83-7.75 (m, 2H), 7.64-7.57 (m, 2H), 7.42-7.35 (m, 2H); ESIMS m/z 386 ([M+21-1 ]+).

The synthetic route of 103962-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Goldsmith, Miriam E.; Knueppel, Daniel I.; (66 pag.)US2016/24027; (2016); A1;,
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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. 1094759-93-9, name is 4-Chloro-5-fluoro-2-iodoaniline, A new synthetic method of this compound is introduced below., Product Details of 1094759-93-9

To Intermediate 5 A (47g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice water, then solid was filtered-off and washed with petroleum ether to afford 49 g of Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+.

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:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56034; (2013); A1;,
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Application of 755027-18-0, 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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 1-(4-Bromo-3-methoxyphenyl)-1H-pyrazol-3-amine A mixture of 1-bromo-4-iodo-2-methoxybenzene (2.5 g, 7.99 mmol), 3-aminopyrazole (0.797 g, 9.59 mmol), salicylaldoxime (0.219 g, 1.598 mmol), Cu2O (91 mg, 0.479 mmol), and Cs2CO3 (3.9 g, 11.98 mmol) in DMF (8 mL) was degassed with N2 and heated at 95 C. overnight. After cooling to RT, the mixture was filtered through celite and rinsed with EtOAc. The filtrate was washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (10%-60% EtOAc in Heptane) to give 1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-amine (800 mg, MS: 270.3 [M+H+]).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-iodo-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; AXFORD, Jake; DALES, Natalie; SUNG, Moo Je; US2014/206661; (2014); A1;,
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31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, 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. Formula: C8H9I

Example 21 – Synthesis of 6,13-Bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro- decyldiisopropylsilylethvnyl)-2-pentafluoroethylpentacene Synthesis of 1,2-Dimethyl-4-pentafluoroethylbenzeneInto a nitrogen purged, flame dried round bottom flask was added 4-iodo-o-xylene (15.0 g, 64.7 mmol), sodium pentafluoropropionic acid (16.8 g, 90.5 mmol), copper (I) iodide (12.3 g, 64.6 mmol) and 100 mL of anhydrous N-methylpyrrolidinone. The reaction mixture was heated at 170C for 16 hours, then cooled to room temperature, and run through a thick silica gel plug with hexane. The collected yellow liquids were then evaporated to dryness on a rotary evaporator, and the oil distilled at 60C (10 ‘ Torr) to collect the desired product (9.14 g, 63%) as a colorless liquid. Analysis of the product provided the following data: 1H NuMR (200 MHz, CDCl3) delta = 2.347 (s, 6H), 7.247 (d, J= 7.8 Hz, IH), 7.357 (s, IH), 7.401 (s, IH). 13C NuMR (50 MHz, CDCl3) delta = 19.810, 19.840, 124.013 (t, J= 6.1 Hz), 127.472 (t, J = 6.1 Hz), 130.158, 137.563, 141.205. GC-MS: m/z: 224 (Ci0H9F5).

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

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; OUTRIDER TECHNOLOGIES; CLOUGH, Robert, Steven; ANTHONY, John, E.; FLYNN, Richard, M.; MOORE, George, G.I.; PAYNE, Marcia, M.; WO2010/138807; (2010); A1;,
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Related Products of 51411-81-5,Some common heterocyclic compound, 51411-81-5, name is 3-Amino-4-iodobenzoic acid, molecular formula is C7H6INO2, 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.

3-Amino-4-iodobenzoic acid (13.35 g, 50.8 MMOL) was added to MEOH (150ML) and SOCI2 (4.8 mL, 65.8 MMOL, 1.3 equivalent) was added. The mixture was REFLUXED for 3 h and then volatiles were removed under reduced pressure. The residue was co- evaporated 3 x with MEOH and dried in vacuo (15.23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-iodobenzoic acid, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/65367; (2004); A1;,
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41252-95-3, name is 1-Chloro-4-iodo-2-nitrobenzene, 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. Application In Synthesis of 1-Chloro-4-iodo-2-nitrobenzene

General procedure: A mixture of aryl iodide (5) (1.0 mmol), PdCl2(PPh3)2(5.0 mol%), CuI (10 mol%), and Et3N (2 mmol, 0.3 mL) was stirred in CH3CN (3 mL) at room temperature for 20 minunder an argon atmosphere. 4-Methyl-2-(methylthio)-6-(prop-2-yn-1-yloxy)pyrimidine (3) (1.0 mmol, 0.19 g), wasthen added and the mixture was stirred at room temperature.After completion of the reaction, the crude product was subjected to flash column chromatography (hexane/ethyl acetate = 10:1) to afford the pure product (see Table 2).

The synthetic route of 41252-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rezaeimanesh, Fatemeh; Bakherad, Mohammad; Nasr-Isfahani, Hossein; Journal of Chemical Research; vol. 43; 9-10; (2019); p. 431 – 436;,
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These common heterocyclic compound, 755027-21-5, name is 4-Chloro-1-iodo-2-methoxybenzene, 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. Product Details of 755027-21-5

Example 60A 4-CHLORO-2-METHOXYBENZONITRILE A mixture of Example 59A (2.68g, 10 mmol), Zn (CN) 2 (0.654g, 5.5 mmol), and Pd (PPh3) 4 (0. 577G, 0.5 mmol) in DMF (15 mL) was stirred at 90 C for 6 hours and cooled to room temperature. The reaction mixture was poured into water (500 ML) and extracted with ethyl acetate several times. The combined extracts were washed with water and brine, dried (MGS04), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9: 1 hexanes/ethyl acetate to provide 1.34g (90%) of the desired product. MS (DCI) m/e 168 (M+H) ; H NMR (300 MHz, CDC13) 8 7.49 (d, J = 8.1 Hz, 1H), 6.97-7. 03 (m, 2H).

The synthetic route of 4-Chloro-1-iodo-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
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Related Products of 33994-44-4,Some common heterocyclic compound, 33994-44-4, name is Methyl 3-(4-Iodophenyl)propanoate, molecular formula is C10H11IO2, 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.

A 500 ml three-neck flask is charged with 20.5 g of 4-(2-thienyl)-iodobenzene, 15.0 g of 4-[2-(5-chloro)-thienyl]-acetoanilide, 12.4 g of potassium carbonate, 0.8 g of copper sulfate pentahydrate and 60 ml of o-dichlorobenzene, and the mixture is stirred under heating at 180 C. for 15 hours in a nitrogen stream. After this reaction, 100 ml of ethylene glycol and 5.1 g of potassium hydroxide are added to the reaction mixture, which is then refluxed under heating for 3 hours in a nitrogen stream, then cooled to ambient temperature, poured into 300 ml of distilled water and neutralized by hydrochloric acid to thereby precipitate crystals. The crystals are filtered, sufficiently washed with water and then transferred to a 1 L flask. To the crystals are added 500 ml of toluene, followed by refluxing under heating to remove water by azeotropic distillation. Then, 100 ml of methanol and 1 ml of concentrated sulfuric acid are added and the resulting mixture is refluxed under heating for 2 hours in a nitrogen stream. After the reaction, the reaction solution is dissolved in distilled water and extracted with toluene. The organic phase is sufficiently washed with distilled water. Next, the organic phase is dried by sodium sulfate anhydride, a solvent is evaporated off under reduced pressure and the residue is recrystallized from an ethyl acetate-hexane mixed solution to obtain 14.2 g of diarylamine. A 100 ml flask is charged with 6.0 g of the thus obtained diarylamine, 5.7 g of methyl 4-iodophenylpropionate, 3.4 g of potassium carbonate, 0.2 g of copper sulfate pentahydrate and 15 ml of o-dichlorobenzene, and the mixture is refluxed under heating for 9.5 hours in a nitrogen stream. After the reaction is completed, the reaction mixture is cooled to ambient temperature and dissolved in 100 ml of toluene, and unnecessary substances are removed by filtration. An obtained filtrate is purified by silica gel column chromatography using toluene, to thereby yield 5.6 g of a chloro compound of triarylamine. Next, a 100 ml eggplant-shape flask is charged with 1.3 g of nickel chloride anhydride, 10.5 g of triphenylphosphine and 50 ml of DMF, and the mixture is stirred under heating. When the temperature of the reaction solution is 50 C., 0.7 g of zinc (powder) is added thereto, which is then stirred under heating at 50 C. for 1 hour. Thereafter, 5.3 g of the chloro compound of triarylamine is added to the reaction mixture, which is then stirred under heating at 50 C. for 0.5 hours. After the reaction is completed, the reaction solution is cooled to ambient temperature and poured into 500 ml of distilled water, followed by vigorous stirring. The precipitated crystals are collected by suction filtration and washed with distilled water to obtain a crude product. The obtained crude product is purified by silica gel column chromatography using hexane/ethyl acetate. Thus, 6.4 g of a thiophene-containing compound (Exemplary Compound 48) is obtained. A melting point of the obtained thiophene-containing compound is 103 to 105 C. An IR spectrum (obtained using a KBr tablet method) of the thiophene-containing compound is shown in FIG. 8. An 1H-NMR spectrum (in a CDCl3 solvent) of the thiophene-containing compound is shown in FIG. 9.

The synthetic route of 33994-44-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ohba, Yoshihiro; Sato, Kazuaki; Seki, Mieko; Agata, Takeshi; Sato, Katsuhiro; Mashimo, Kiyokazu; Yoneyama, Hirohito; Hirose, Hidekazu; US2005/59730; (2005); A1;,
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Electric Literature of 2401-21-0,Some common heterocyclic compound, 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, molecular formula is C6H3Cl2I, 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.

Method C 2,3-Dichloroiodobenzene (350 g, 1.282 mol) dissolved in dry ether (1250 ml) was added slowly, with stirring, to magnesium turnings (30.77 g, 1.282 mol) in dry diethyl ether (300 ml), in order to form 2,3-dichlorophenylmagnesium iodide under nitrogen.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dichloro-3-iodobenzene, its application will become more common.

Reference:
Patent; Glaxo Wellcome Inc.; US5925755; (1999); A;,
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Electric Literature of 216393-67-8,Some common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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 solution of the substituted 2-iodoaniline or 2-bromoaniline (1.0 equiv), DMAP (0.05 equiv) and NEt3 (2.0 equiv) was prepared in CH2Cl2 (2mL) and cooled to 0 C. The acyl chloride solution was added dropwise into the solution. After 5 minutes, the reaction was allowed to warm to room temperature and was stirred overnight. The reaction was quenched with a saturated NaHCO3 solution and extracted with CH2Cl2 twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting crude amide was used in next step without further purification.

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-fluoro-6-iodoaniline, its application will become more common.

Reference:
Article; Xiao, Genhua; Chen, Liang; Deng, Guobo; Liu, Jianbing; Liang, Yun; Tetrahedron Letters; vol. 59; 19; (2018); p. 1836 – 1840;,
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