Iodides-buliding-blocks

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. 624-75-9 name is 2-Iodoacetonitrile, 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. 624-75-9

A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 120a (6.70 g, 37.4 mmol), iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture over the period of 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfate heptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C. to 35 C., until the color of the reaction mixture was deep red. When TLCs showed the reaction was not complete, more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalents) were added in the same manner until the reaction was complete. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with saturated sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 120b as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J=6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J=6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodoacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

25252-00-0, Adding a certain compound to certain chemical reactions, such as: 25252-00-0, name is 2-Bromo-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 25252-00-0.

General procedure: To a solution of 0.5 g compound 3(0.10 mol) in 3 ml DMF, 3.3 mg (0.01 mol) of copper iodide, 0.57 gcesium carbonate (0.1 mol), 20 mg (0.01 mol) Tetrakis (triphenylphosphine)palladium(0) was added under nitrogen atomophere. Then arylhalide (4-12) 0.11 mol was added under nitrogen atm, the mass wasstirred for 8 hrs at 75 C under nitrogen atm. Reaction was completed asindicated by TLC and the reaction mass was filtered through cellite bed,washed the bed with ethyl acetate (10 ml). The product layer (Ethylacetate layer)was then washed with water 10.0 ml, sodium bi sulphite10 ml followed by saturated sodium chloride solution (5.0 ml) and driedover (Na2SO4). The solvent was distilled off and the resulting productwas purified by column chromatography using ethyl acetate and nhexaneto get the pure product (4a-l). Yield observed was around85-90% for all the derivatives.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thangarasu; Thamarai Selvi; Manikandan; Bioorganic Chemistry; vol. 81; (2018); p. 468 – 480;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

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

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
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

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

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

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

A common compound: 624-75-9, name is 2-Iodoacetonitrile, 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. 624-75-9

j181j To a mixture of 5-bromo-2-isopropyl-4-methoxy-phenol from step 4 (0.831 g, 3.4 mmol) and K2C03 (0.562 g, 4.1 mmol) in 17 mL dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in 50 mL of H20 and extracted with 1:1 toluene/ethyl acetate, washed with H20 and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2C12) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.611 g, 63%) as a while solid.

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, 624-75-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AFFERENT PHARMACEUTICALS, INC.; FORD, Anthony P.; PATON, Julian; (86 pag.)WO2016/4358; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 610-97-9, name is Methyl 2-iodobenzoate, molecular formula is C8H7IO2, 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. 610-97-9.

To a solution of methyl 2-iodobenzoate in a 2:1 mixture of drytetrahydrofuran/triethylamine was added Pd(PPh3)4 (6 mol %) followed by CuI (3mol %) and propargyl alcohol (3 equiv), under argon atmosphere. The above solutionwas stirred at 40 C and the reaction progress was monitored by TLC. After completion,the reaction mixture was concentrated in vacuo and the crude residue was purifiedthrough flash column chromatography to obtain the cross-coupled products

The synthetic route of Methyl 2-iodobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Bin; Shi, Bing-Feng; Synlett; vol. 27; 16; (2016); p. 2396 – 2400;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

4028-63-1, Adding some certain compound to certain chemical reactions, such as: 4028-63-1, name is 2,4,6-Trimethyliodobenzene, 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 4028-63-1.

General procedure: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1molpercent), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 ¡ãC (X=I) or 130 ¡ãC (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.

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 4028-63-1.

Reference:
Article; Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Liu, Yang; Ning, Shunhua; Tetrahedron Letters; vol. 55; 51; (2014); p. 7121 – 7123;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com