Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 19094-56-5, 19094-56-5

A 2 L three-necked round bottom flask with mechanical stirrer, rubber septum with temperature probe and pressure-equalized addition funnel with gas bubbler was charged with 2-chloro-5-iodobenzoic acid (199.41 g, 0.706 mol), dichloromethane (1.2L, KF=0.003 wt % water) and the suspension was set stirring at ambient temperature. Then N,N-dimethylformamide (0.6 mL, 1.1 mol %) was added followed by oxalyl chloride (63 mL, 0.722 mol, 1.02 equiv) which was added over 11 min. The reaction was allowed to stir at ambient overnight and became a solution. After 18.75hours, additional oxalyl chloride (6 mL, 0.069 mol, 0.10 equiv) was added to consume unreacted starting material. After 2 hours, the reaction mixture was concentrated in vacuo to afford crude 2-chloro-5-iodobenzoyl chloride as a pale yellow foam which will be carried forward to the next step.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Goodwin, Nicole Cathleen; Harrison, Bryce Alden; Iimura, Shinya; Mabon, Ross; Song, Qiuling; Wu, Wenxue; Yan, Jie; Zhang, Haiming; Zhao, Matthew Mangzhu; US2009/30198; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 94 2-Amino-5-iodobenzyl alcohol STR205 A solution of diisobutylaluminium hydride (210 cm3 of a 1.5M solution in THF) was added at -30 to a stirred solution of methyl-2-amino-5-iodobenzoate (28.0 g) in THF (100 cm3) under nitrogen. The mixture was warmed to room temperature, stirred for 16 hours and treated with methanol (35 cm3). Ethyl acetate (500 cm3) was added and the mixture filtered to remove inorganic material. The filtrate was concentrated in vacuo to afford a solid which was chromatographed on silica (Merck “MK 60.9385”) eluding wiht chloroform:methanol, 49:1 (by volume), and the requisite fractions were combined and evaporated in vacuo to give 2-amino-5-iodobenzyl alcohol, m.p. 125, (19.0 g). Analysis %: Found: C, 34.4; H, 3.2; N, 6.0; Calculated for C17 H8 INO: C, 33.8; H, 3.2; N, 5.6.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Pfizer Inc.; US4710507; (1987); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, Adding some certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 19094-56-5.

A. 2-Chloro-5-iodo-benzoyl chloride. A stirring solution of 2-chloro-5-iodo-benzoic acid (12.4 g, 43.9 mmol) in SOCl2 (40 mL, 550 mmol) was heated to reflux under a N2 atmosphere. After 20 h, the mixture was concentrated to give the product (13.2 g, 100%) as a yellow solid. 1H NMR (d6-DMSO): 7.88 (s, 1H), 7.65 (dd, J=8.4, 2.0, 1H), 7.14 (d, J=8.4, 1H).

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 19094-56-5.

Reference:
Patent; Ameriks, Michael K.; Axe, Frank U.; Edwards, James P.; Grice, Cheryl A.; Cai, Hui; Gleason, Elizabeth Ann; Meduna, Steven P.; Tays, Kevin L.; Wiener, John J. M.; Wickboldt, Alvah T.; US2008/200454; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene, A new synthetic method of this compound is introduced below.

5-Bromo-2-iodotoluene (0.144 mL, 1.01 mmol), pyrazole (68.8 mg, 1.01 mmol), copper(I) oxide (7.2 mg, 0.051 mmol), (15,,2lS,)-bis(pyridin-2-ylmethylene)cyclohexane-l,2- diamine (59.1 mg, 0.202 mmol), and cesium carbonate (658 mg, 2.02 mmol) were combined in a sealed microwave vial, and dissolved in acetonitrile (1.4 mL). The reaction was stirred at 82C overnight and then cooled to room temperature and filtered through Celite, rinsing the Celite pad with dichloromethane. The solution was concentrated in vacuo and the crude material was purified by silica chromatrography, eluting with a gradient of 0-25% ethyl acetate in hexanes. LRMS (ESI) calc’d for Ci0Hi0N2Br [M+H] +: 237, 239 (1 : 1), found 237, 239 (1 : 1). 1H NMR (500 MHz, CDC13): delta 7.72 (s, 1H), 7.57 (s, 1H), 7.47 (s, 1H), 7.40 (d, / = 8.0 Hz, 1H), 7.19 (d, / = 8.5 Hz, 1H), 6.44 (s, 1H), 2.22 (s, 3H).

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation 49 Methyl 5-Iodo-2-((methylsulfonyl)amino)benzoate [BW.2] To a solution of 5-iodoanthranilic acid methyl ester (1.00 g) and triethylamine (1.01 mL) in CH2Cl2 (25 mL) is added methanesulfonyl chloride (0.59 mL) at 0 C. The ice bath is removed and after 3 h at room temperature the solution is poured into water (20 mL) and extracted with CH2Cl2 (2*20 mL). The organic layers are combined, dried over MgSO4 and the solvent removed in vacuo. The resulting residue is dissolved in CH3OH (20 mL) and sodium methoxide (20 mL) is added. After 45 min, the solvent is removed in vacuo. The residue is diluted with Et2O (20 mL) and washed with water (20 mL). The organic layer is separated, dried over MgSO4, filtered, and concentrated in vacuo. The crude black liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc) to afford 0.58g (46%) of the title compound as a brown solid. Physical characteristics: m.p. 119-120 C.; 1H NMR (300 MHz, CDCl3) delta 10.41, 8.36, 7.82, 7.52, 3.94, 3.06; IR (diffuse reflectance) 1700, 1682, 1483, 1385, 1335, 1328, 1307, 1249, 1213, 1159, 1147, 1093, 1086, 978, 971 cm-1; MS (FAB) m/z 356 (MH+); HRMS (FAB) m/z 355.9447 (C9H10INO4S+H). Anal. Found: C, 30.49; H, 2.88; N, 3.96.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bundy, Gordon L.; Ciske, Fred L.; Genin, Michael J.; Heasley, Steven E.; Larsen, Scott D.; Lee, Byung Hyun; May, Paul D.; Palmer, John R.; Schnute, Mark E.; Vaillancourt, Valerie A.; Thorarensen, Atli; Wolf, Allison J.; Wicnienski, Nancy Anne; Wilhite, David; US2002/25960; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 696-41-3, name is 3-Iodobenzaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 696-41-3. 696-41-3

General procedure: Aryl iodide 3 (0.2 mmol, 1.0 equiv), acrylate/styrene 4 (0.202 mmol, 1.01 equiv), DIPEA (28.4 mg, 0.22 mmol, 1.1 equiv), and Pd(I)-iodo dimer 2 (1.3 mg, 0.0015 mmol, 0.75 mol%) were weighed into a 4 mL screw cap vial, purged with argon, and dissolved in anhydrous toluene(1.5 mL). The vial was capped with a PTFE-lined screw cap and sealed with PTFE tape prior to heating to 100 C under stirring by using an aluminum heating block outside the glovebox. After 15 h, the reaction mixture was allowed to cool to r.t. and diluted with EtOAc (to 20 mL); excess base was quenched by the addition of sat. aq NH4Cl (20 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (2*20 mL). The combined organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography.

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 3-Iodobenzaldehyde.

Reference:
Article; Sperger, Theresa; Stirner, Christopher K.; Schoenebeck, Franziska; Synthesis; vol. 49; 1; (2017); p. 115 – 120;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

612-55-5, A common compound: 612-55-5, name is 2-Iodonaphthalene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a Schlenk tube were added aryl iodides 1 (0.2 mmol, 1.0 equiv),1,2-diphenylethynes 2 (0.2 mmol, 1.0 equiv), 2-bromobenzoic acid 3 (0.24 mmol, 1.2equiv), PdCl2(dppf) (0.01 mmol, 5 mol %), K2CO3 (0.6 mmol, 3.0 equiv), Me4NOAc(0.6 mmol, 3.0 equiv), and DMSO (0.2 M, 1 mL). Then the tube was charged with nitrogen, and was stirred at 140 oC (oil bath temperature) for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the reaction was finished, the resulting suspension was filtered and washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure and purifiedon a silica-gel column chromatography (petroleum ether/EtOAc) to give product 4.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Iodonaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Deng, Guobo; Liang, Yun; Luo, Xiai; Yang, Xiumei; Yang, Yuan; Yang, Yuzhong; Zhou, Liwei; Synthesis; vol. 52; 8; (2020); p. 1223 – 1230;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5326-47-6, These common heterocyclic compound, 5326-47-6, name is 2-Amino-5-iodobenzoic acid, 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.

Concentrated H2SO4 (3.7 mL) was added dropwise at 20 C under argon atmosphere to a stirred solution of 5-iodoanthranilic acid (5.0 g, 19 mmol) in MeOH (20 mL), and the mixture was refluxed for 7 h. The mixture was then concentrated in vacuo to the volume of 10 mL, poured into a vigorously stirred saturated solution of NaHCO3 (80 mL), and extracted with EtOAc. The organic layer was washed with a brine solution, dried over Na2SO4, and concentrated in vacuo; the residue was purified by chromatography on SiO2 (eluent was benzene). Ester 6 (3.68 g) was isolated as yellow crystals, m.p. 80-82 C (LP). 1H NMR (CDCl3), delta: 3.87 (s, 3 H, MeO); 5.76 (br.s, 2 H, H2N); 6.46 (d, 1 H, HC(3), J = 8.7 Hz); 7.48 (dd, 1 H, HC(4), J = 8.7 Hz, J = 2.2 Hz); 8.14 (d, 1 H, 2 HC(6), J = 2.2 Hz); which is similar to that reported previously.24

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 5326-47-6.

Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

698-70-4, A common heterocyclic compound, 698-70-4, name is 4-Iodo-N,N-dimethylaniline, molecular formula is C8H10IN, 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 the solution of 4-iodo-N,N-dimethylaniline2 (1.235 g, 5 mmol) in THF (15 mL), 2-methyl-3-butyn-2-ol (0.6 mL, 6 mmol) and diisopropylamine (2.1 mL, 15 mmol) was added. After stirring the solution under argon at 70 C for 20 min, copper(I) iodide (100 mg, 0.5 mmol) and triphenylphosphine (144 mg, 0.6 mmol) were added. After both reagents have dissolved, palladium(II) acetate (8 mg, 0.035 mmol) was added and stirring was continued for 5 h. Upon cooling, the reaction mixture was filtered and the filtrate was extracted by CH2Cl2. The organic layer was washed with water, dried with sodium sulphate, filtered, and concentrated by rotary evaporation. The crude product was purified by radial chromatography (silica gel, EtOAc/PE = 1/10) to give 4-[4-(dimethylamino)phenyl]-2-methylbut-3-yn-2-ol3 (586 mg, 57%) as yellow crystals: mp 83.0 – 86.5 C. 1H NMR (300 MHz, CDCl3 ) delta (ppm) 1.53 (s, 1H), 1.6 (s, 6H); 2.9 (s, 6H); 6.6 (d, 2H); 7.3 (d, 2H). IR [cm-1] 3329, 2979, 2931, 2222, 1609, 1518.

The synthetic route of 698-70-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rejc, Luka; Fabris, Jan; Adrovi?, Armin; Kasuni?, Marta; Petri?, Andrej; Tetrahedron Letters; vol. 55; 6; (2014); p. 1218 – 1221;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 696-41-3 name is 3-Iodobenzaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 696-41-3

General procedure: As outlined in Schemes 1 and 2, under anhydrous andanaerobic conditions, ZnCl2 (0.05 mol) was added to themixture of resorcinol (0.1 mol) and chloroacetonitrile (0.12mol) in diethyl ether (50 mL) cooled to 0C. The mixturewas reacted with anhydrous hydrogen chloride gas for 12hours. Intermediate compound 1, chrysin derivatives 2-5were synthesized according to Scheme 2. The Baker-VenKataraman reaction was employed in the synthesis ofchrysin derivatives [31]. 2, 4-dihydroxybenzoyl chloride (86mmol) was obtained after recrystallization with water. 2-Iodobenzaldehyde, 3-iodobenzaldehyde, 2-fluorine-5-iodobenzaldehyde or 3-iodo-4,5-dimethoxy benzaldehyde(12 mmol) and 10% NaOH (20 mL) were added to a solutionof compound 1 (10 mmol) in alcohol (5 mL). The mixturewas stirred at room temperature for 72 hours. Then the solutionwas acidified with 10% aqueous HCl to pH= 7 andstirred for another 48 hours at room temperature. The crudeproduce was purified by column chromatography (ethylacetate/ petroleum ether = 1:1) to get products, compound2: 7-hydroxy-2-(2-iodophenyl)-4H-chromen-4-one yielded62.7%, compound 3: 7-hydroxy-2-(3-iodophenyl)-4Hchromen-4-one yielded 61.5%, compound 4: 2- (2-fluoro-5-iodo- phenyl)-7-hydroxy-4H-chromen-4-one yielded 60.8%,compound 5:7-hydroxy-2-(3- iodo-4,5-di- methoxyphenyl)-4H-chromen-4-one yielded 62.3%. All compounds were yellow products.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodobenzaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Wei, Yun; Zheng, Qutong; Tang, Guotao; Song, Chen; Wang, Guan; Zhang, Yinxiang; Xiao, Yan; Zeng, Xianliang; Wang, Zongbao; Xiao, Jichang; Zheng, Xing; Medicinal Chemistry; vol. 12; 5; (2016); p. 441 – 447;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com