Month: September 2021

Electric Literature of 105202-02-6, 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. 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PdCl2(PPh3)2 (35.1 mg, 0.05 mmol), CuI (9.5 mg, 0.05 mmol), PPh3 (13.1 mg, 0.05 mmol) and iodoaniline derivatives (1.00 mmol) were stirred under N2 in a mixed solvent with CH3CN (5 mL) and Et3N (1 mL). The alkyne (1.20 mmol) was added to the mixture and stirred in reflux. The reaction was monitored by TLC. After completion, H2O (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over anhydrous MgSO4, concentrated at the reduced pressure. And the crude product was purified by column chromatography to give 2-alkynylanilines.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-5-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Sheng-Yan; Sun, Shan-Gang; Guo, Yu-Shuang; Lu, Xiao-Fan; Guo, Dian-Shun; Tetrahedron Letters; vol. 59; 41; (2018); p. 3719 – 3723;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 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.

The synthesis of (cyanomethyl)trimethylphosphonium iodide is carried out in very much the same way as the procedure described in the literature [J. Org. Chem. 2001, 66, 2518-2521] from trimethylphosphine and iodoacetonitrile. 2.42 g of (cyanomethyl)trimethylphosphonium iodide is added to a solution of 1 g of alcohol 8 in 18 ml of propionitrile, and then 2.1 ml of diisopropyl ethylamine is added in drops. The reaction mixture is stirred for 14 hours at 97 C. After cooling to room temperature, the batch is mixed with 10 ml of water and 1 ml of concentrated hydrochloric acid. The phase separation is carried out between ethyl acetate/water. The organic phase is washed with water and saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. Column-chromatographic purification (cyclohexane/ethyl acetate) yields 480 mg of cyanide 11b as a colorless foam (GC-MS: m/z theor.: 535, pract.: 535).

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Braeuer, Nico; Peters, Olaf; Hillisch, Alexander; Bohlmann, Rolf; Richter, Margit; Muhn, Hans-Peter; US2005/65135; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2142-70-3, 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. 2142-70-3, name is 1-(2-Iodophenyl)ethanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: (0013) A mixture of aryl halide (1 equiv), Cu(0) powder (10 equiv), and CuTC (2 equiv) in DMSO (0.2 mL/mmol of aryl halide) was stirred at 65-70 C for 15-72 h. Water and EtOAc were added, and the two phases were separated. The aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product which was further purified by preparative TLC (EtOAc/hexanes) to furnish the desired product.

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, 1-(2-Iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yasamut, Kittisak; Jongcharoenkamol, Jira; Ruchirawat, Somsak; Ploypradith, Poonsakdi; Tetrahedron; vol. 72; 40; (2016); p. 5994 – 6000;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5159-41-1, name is 2-Iodobenzyl alcohol, 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. Quality Control of 2-Iodobenzyl alcohol

The reaction was carried out using o-iodobenzyl alcohol (i.e., R1 in the formula (I) o) 1.0 mmol (234.0 mg)The procedure and procedure were the same as in Example 1, aqueous ammonia (1.6 mol / L) 5.0 mL, catalyst copper sulfate was used in an amount of 5 mol% (8.0 mg)TEMPO is used in an amount of 8 mol% (12.5 mg) at a reaction temperature of 120 C and a reaction time of 18 h. The crude product is purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure title product at 206.1 mg yield of 90%.

The synthetic route of 5159-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Zhang Guofu; Zhao Yiyong; Zhang Guihua; Ding Chengrong; Yu Yidong; Lv Jinghui; (10 pag.)CN106866326; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20555-91-3, name is 1,2-Dichloro-4-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. Computed Properties of C6H3Cl2I

Palladium(II) acetate (0.17 g, 0.73 mmol) was added to a mixture of 1,2- dichloro-4-iodobenzene (2.00 g, 7.33 mmol), prop-2-en-l-ol (0.75 mL, 1 1 mmol), benzyltriethylammonium chloride (1.67 g, 7.33 mmol) and sodium bicarbonate (1.54 g, 18.3 mmol) in DMF (5 mL) and the mixture was degassed and back filled with Ar three times. The reaction mixture was heated at 60 C for 2 h. The mixture was diluted with Et20 (15 niL) and H2O (15 niL) and the mixture was filtered through a celite pad. The organic layer was separated and the aqueous layer was extracted with E20 twice. The combined organic layers were dried over MgS04, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0- 10% over 20 min, column 80 g, flow rate 40 mL/min) to give Intermediate 16A (1.0 g, 4.9 mmol, 67 % yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.78 (2 H, t, J=7.3 Hz), 2.91 (2 H, t, J=7.3 Hz), 7.03 (1 H, dd, J=8.2, 2.1 Hz), 7.29 (1 H, d, J=2.3 Hz), 7.35 (1 H, d, J=8.0 Hz), 9.81 (1 H, s).

The synthetic route of 20555-91-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/49096; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7, 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. 460-37-7 name is 1,1,1-Trifluoro-3-iodopropane, 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.

: in a 100 ml dry single-mouth flask, isopropyl 2-bromo-6-methyl-5-(1-(piperazine-1-ethyl)ethyl)indolizine-7-carboxylate hydrochloride (170 mg, 0.38 mmol) was dissolved in N,N-dimethylformamide (10 mL), and 1,1,1-trifluoro-3-iodopropane (170 mg, 0.76 mmol), potassium carbonate (157 mg, 1.14 mmol) were added, the mixture was microwave-stirred at 100 C. for 2 hours, water was added, and extracted with ethyl acetate (50*3 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtrated, and solvent was removed under reduced pressure to give a yellow oil (120 mg, 63%), MS (ESI) m/z 504 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,1-Trifluoro-3-iodopropane, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI HAIHE PHARMACEUTICAL CO., LTD.; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; CHEN, Xuxing; GENG, Meiyu; JIANG, Lei; CHEN, Yi; CAO, Jianhua; JIANG, Qingyun; SHEN, Qianqian; DING, Jian; YAO, Yucai; ZHAO, Zhao; XIONG, Yuanfang; (247 pag.)US2019/211010; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

455-13-0, name is 4-Iodobenzotrifluoride, 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. Product Details of 455-13-0

General procedure: Step 1. To a solution of the arylhalide (1 equiv.) and propargyl alcohol (3 equiv.) in triethylamine (0.2 M) was added Pd(PPh3)4 (1 mol %) and CuI (5 mol %, dissolved in minimum necessary amount of triethylamine) under Ar. The resulting mixture was stirred at ambient temperature. After completion of the reaction, the reaction mixture was diluted with EtOAc and filtered through a short pad of SiO2 (eluent EtOAc). The filtrate was concentrated in vacuo and the crude products were purified by flash column chromatography on silica to afford the propargylic alcohol 13a – 13i.

The synthetic route of 455-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kristianslund, Renate; Aursnes, Marius; Tungen, J°rn Eivind; Hansen, Trond Vidar; Tetrahedron Letters; vol. 57; 47; (2016); p. 5232 – 5236;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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. Formula: C6H3Cl2I

Method B: a mixture of 3,4-dichloroiodobenzene (300 mg), propargyl alcohol (128 muL), CuI (10 mg), K2CO3 (302 mg), Pd(PPh3)4 (12 mg) in DMF (2 mL) was irradiated with MicroWave at 100 0C for 20 min. Aqueous saturated solution NH4CI was then added followed by DCM. After separation of the two phases the organic layer was dried and evaporated in vacuo. The crude product was purified by flash chromatography (eluting with cyclohexane / ethyl acetate 7/3) to give the title compound (40 mg). NMR (1H, CDCI3): delta 7.58 (s, 1 H), 7.41 (d, 1 H), 7.27 (d, 1 H), 4.52 (d, 2H), 1.75 (t, 1 H)

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/31772; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 159217-89-7, A common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, 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.

5 g (15,7 mmol) N-tert-Butyloxycarbonyl-4-iodanilin (BOC-geschuetztes 4-lodanilin) in 30 ml Toluol wurden bei Raumtemperatur mit einer Spatelspitze 4-Dimethylaminopyridin als Katalysator und 5,02 g (23,0 mmol) Di-tertbutyldicarbonat (BOC-Anhydrid) versetzt. Man liessueber Nacht ruehren, verduennte mit 30 ml Dichlormethan, wusch mit 20 ml 5 %iger Salzsaeure, trennte die Phasen und engte die organische Phase bis zur Trockene ein. Der Rueckstand wurde im Hochvakuum von Loesungsmittelresten befreit. Man erhielt das zweifach BOCgeschuetzte 4-lodanilin in 4,41 g (10,5 mmol, 67 %) Ausbeute. Die gesamte Menge wurde in 25 ml THF geloest und zu einer auf -78C gekuehlten Loesung von Lithiumtributylmagnesat in THF/Hexan (ca. 44 ml, 12,6 mmol) getropft (hergestellt aus Butylmagnesiumbromid-Loesung in THF und Butyllithium-Loesung in Hexan bei 0 C). Nach 40 min Nachruehren wurden 3,27 g (31,5 mmol) Trimethylborat langsam zugetropft. Man ruehrte noch 30 min bei -78C nach und liess dann langsam auf 0C erwaermen. Zur Hydrolyse wurden 70 ml 2 N methanolischer Chlorwasserstoff zugegeben und 7 h geruehrt. Zur Isolierung des Produkts gab man das Gemisch in 250 ml Wasser und 250 ml Toluol, extrahierte und trennte die Phasen. Die Toluolphase wurde eingeengt und das Produkt aus Methanol umkristallisiert. Man erhielt 0,64 g (3,7 mmol, 35 %) des 4-Anilinboronsaeure-Hydrochlorids; zusaetzlich war durch Protodeborierung eine nicht bestimmte Menge Anilin entstanden (Ausbeute ueber beide Stufen 23,5 %).

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; Clariant GmbH; EP1479686; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com