Month: January 2021

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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H6BrIO

To a stuffed solution of 1-bromo-4-iodo-2-methoxybenzene (2.4 g, 7.66 mmol) in diethyl ether (25 mL) was added n-BuLi (2M in hexane; 4.40 mL, 8.81 mmol) at -78 C dropwise. The reaction mixture was stuffed at -78 C for 30 mm, and then triisopropyl borate (2.03 mL, 8.81 mmol) was slowly added to the reaction mixture at -78 C. The temperature of the reaction mixture was gradually raised to RT over a period of 1 h, and then the reaction mixture was stirred at RT for 30 mm. After 30 mm, 3 N HC1 (25 mL) was slowly added to the reaction mixture at 0 C and stuffed for 1 h. The progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water (150 mL) and the product was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate and concentrated. The residue obtained was triturated with hexane (2×25 mL) to afford 4-bromo-3-methoxyphenylboronic acid as an off-white solid (1.45 g).

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; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, 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 689291-89-2, COA of Formula: C7H4BrIO

Compound 12 (32 mg, 0.10 mmol), 41 (55.6 mg, 0.103 mmol), PdCl2(PPh3)2 (3.6 mg, 0.0051 mmol), and CuI (1.96 mg, 0.0103 mmol) were added to Et3N (6 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt under N2 protection for 3 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 51, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 7:3) to yield compound 51 (60 mg, 0.083 mmol, 81%) as a white solid. Mp 82-83 C; IR (KBr) 2918, 2851, 2207, 1690, 1631, 1603, 1583, 1552, 1533, 1513, 1497, 1469, 1420 cm-1; 1H NMR (CDCl3, 500 MHz) delta 10.66 (s, 1H), 8.07 (d, J=1.5 Hz, 1H), 7.69 (dd, J=8.0, 1.5 Hz, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.60 (d, J=8.5 Hz, 2H), 7.49 (d, J=8.0 Hz, 1H), 7.02 (s, 1H), 7.01 (s, 1H), 4.05-4.01 (m, 4H), 1.89-1.83 (m, 4H), 1.60-1.46 (m, 4H), 1.30-1.26 (m, 24H), 0.89-0.86 (m, 6H); 13C NMR (CDCl3, 125 MHz) delta 190.9, 154.3, 154.0, 137.2, 136.8, 134.3, 132.24, 132.20, 130.3, 128.5, 125.9, 123.4, 118.7, 116.7, 116.4, 114.1, 113.5, 111.8, 94.3, 93.8, 90.5, 90.2, 69.8, 69.6, 32.1, 29.9, 29.82, 29.76, 29.6, 29.5, 29.4, 26.3, 22.9,14.3; HRMS (CI) m/z calcd for C44H52BrNO3 721.3131, found 722.3139 [M+H]+.

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, 5-Bromo-2-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13194-68-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13194-68-8 as follows.

EXAMPLE 1 4-Fluoro-2-(4-iodo-2-methylphenylamino)benzoic acid To a stirring solution comprised of 3.16 g (0.0133 mol) of 2-amino-5-iodotoluene in 5 mL of tetrahydrofuran at -78 C. was added 10 mL (0.020 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethenylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 15 minutes, after which time a solution of 1.00 g (0.00632 mol) of 2,4-difluorobenzoic acid in 10 mL of tetrahydrofuran was added. The reaction temperature was allowed to increase slowly to room temperature, at which temperature it was stirred for 2 days. The reaction mixture was concentrated. Aqueous HCl (10%) was added to the concentrate, and the solution was extracted with dichloromethane. The organic phase was dried (MgSO4) and then boiled over a steambath to low volume and cooled to room temperature. The off-white fibers were collected by vacuum filtration, rinsed with hexanes, and vacuum-oven dried. (76 C.; ca. 10 mm of Hg) to afford 1.10 g (47%) of the desired material; mp 224-229.5 C.; 1H NMR (400 MHz; DMSO): Lambda 9.72 (s, 1H), 7.97 (dd, 1H, J=7.0, 8.7 Hz), 7.70 (d, 1H, J=1.5 Hz), 7.57 (dd, 1H, J=8.4, 1.9 Hz), 7.17 (d, 1H, J=8.2 Hz), 6.61-6.53 (m, 2H), 2.18 (s, 3H); 13C NMR (100 MHz; DMSO): Lambda 169.87, 167.60, 165.12, 150.17, 150.05, 139.83, 138.49, 136.07, 135.31, 135.20, 135.07, 125.60, 109.32, 105.09, 104.87, 99.72, 99.46, 89.43, 17.52; 19F NMR (376 MHz; DMSO): delta-104.00 to -104.07 (m); IR (KBr) 1670 (C=O stretch) cm-1; MS (CI) M+1=372. Analysis calculated for C14H11FINO2: C, 45.31; H, 2.99; N, 3.77. Found: C, 45.21; H, 2.77; N, 3.64.

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US6310060; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-76-0, name is 2-Iodoethanol, 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 624-76-0, category: iodides-buliding-blocks

To the mixture of 4-iodopyridin-2(1H)-one (50 mg, 0.213 mmol) in DMF (3 mL) was added 2-iodoethanol (73 mg, 0.426 mmol), K2CO3 (88 mg, 0.638 mmol) at rt. The mixture was stirred for 2 h at rt. After the reaction was finished, the mixture was washed with water and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated to give the crude product, which was purified by TLC to provide 1-(2-hydroxyethyl)-4-iodopyridin-2(1H)-one (60 mg 100%).

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-Iodoethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, 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 455-13-0, Quality Control of 4-Iodobenzotrifluoride

Add in a 50 mL autoclave, add 5 mL of toluene, 1 mmol of 4-trifluoromethyliodobenzene, 1.2 mmol of phenylacetylene, 2.0 mmol of triethylamine, 0.5 mol% of benzimidazole, azacyclocarbene palladium Metal complex (relative to iodobenzene).The reactor was sealed, and the reactor was replaced three times with carbon monoxide to seal the reactor. The pressure of the CO gas was 2.0 MPa, and the temperature was slowly raised to 100 C by the temperature controller. The reaction was carried out for 18 hours, cooled to room temperature, and the kettle was discharged. The liquid obtained by the reaction was qualitatively analyzed by an Agilent 6890/5973 GC/MS.Target product1-(4-trifluoromethylphenyl)-3-phenyl-2-propyn-1-oneThe selectivity is greater than 99% and the isolated yield is 95%.

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; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute; Liu Jianhua; Wang Bingyang; Yang Lei; Xia Chungu; Xu Chuanzhi; Zhao Kang; (22 pag.)CN109810147; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 112671-42-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 112671-42-8 as follows.

Under nitrogen conditions, 7H-dibenzo[c,g]carbazole (12.8 g, 47.8 mmol),4-bromo-1-iodo-2-nitrobenzene (17.2 g, 52.6 mmol), cesium carbonate (13.8 g, 71.7 mmol) was stirred in a solvent of dimethyl sulfoxide. After stirring at room temperature for about 2 hours, Raise the temperature to 60 C and stir for 8 hours. Extracted three times with dichloromethane and deionized water, after rotary evaporation, dry over anhydrous MgSO4 and recrystallize the compound from dichloromethane/methanol.Intermediate 1-1 (19 g, 85%) was obtained.

According to the analysis of related databases, 112671-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jilin Aolaide Optoelectric Materials Co., Ltd.; Suo Hongguang; Wang Jinzheng; Jiang Zhiyuan; He Jinxin; Jiang Xiaochen; Jin Furong; (15 pag.)CN109422757; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

461-17-6, name is 1,1,1-Trifluoro-4-iodobutane, 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 1,1,1-Trifluoro-4-iodobutane

The alcohol of Example A12 (0.50 g, 1.23 mmol), tetrabutylammonium bromide (79 mg, 0.246 mmol), and KOH (207 mg, 3.69 mmol) were slurried in xylene (5 mL). Afterward, 4,4,4-trifluoromethyl-1-iodobutane (0.88 g, 3.69 mmol) was added, and the resulting mixture was stirred in a sealed vial at 80 C. over the weekend. Subsequently, the mixture was filtered through celite and concentrated under N2. Chromatography (on silica, ethyl acetate/hexanes) afforded the ether in the form of a colorless oil (296.4 mg, 46.7% yield). NMR(CDCl3) delta 1.25-1.42 (m, 7H), 1.52 (s, 9H), 1.55 (d, 2H), 1.67 (d, 2H), 1.75-1.84 (m, 2H), 2.06-2.24 (m, 4H), 2.32 (d, 2H), 2.92 (t, 2H), 3.40 (t, 2H), 3.38 (t, 2H), 3.43 (t, 2H), 3.72-3.82 (m, 2H), 3.95 (dd, 2H). ESMS m/z=516.44 (M+H)+.

The synthetic route of 461-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 191348-14-8, 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. 191348-14-8, name is 2-Iodo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 ¡Á 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).

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

Reference:
Article; Liu, Lei; Zhu, Ning; Gao, Min; Zhao, Xiaole; Han, Limin; Hong, Hailong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 5; (2016); p. 699 – 701;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 723294-75-5, 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. 723294-75-5 name is 3-Fluoro-5-iodobenzonitrile, 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.

Procedure for preparation of compound 2:To a solution of 13 (1000mg, 0.46mmoi) and 14 (135.8mg, 0.SSmmoi) in DMSO (2OmL) was added CuT (95mg, 0.OSmmol) and C52C03 (399.7mg, 0.92mmoi) at rt, the mixture was stirred at 100C for lOh under N2 atmosphere. The solution was diluted with EtOAc (lOmL), washedwith water, biine (iOmnL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by prep-TLC to afford the target product Compound 2 (5.0mg, yield:3.2 % LCMS: m/z, 338.0 ?M+H)1INNIR (400 MHz, CDCI3): .59 (d, j:::: 4.4 Hz, 111), 7.88 (d, j:::: 6.8 Hz, 1H), 759-752(m, 3H), 750-745 (m, 3H), 7.32-7.28 (m, 3H), 7.19-7.17 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-5-iodobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; LI, Yongguo; (44 pag.)WO2017/173604; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16355-92-3, A common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, 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.

3,3′-(1,9-Decanediyn-1,10-diyl)-bis-pyridine (1 mmol) and an equivalent of 1,10-diiododecane were mixed in acetonitrile (1000 mL). The mixture was refluxed for 7 days. The solvent was removed in vacuo after cooling and the resulting residue was taken up in water and partitioned between diethyl ether and water. The aqueous layer was extracted extensively with diethyl ether remove the starting materials. Most of the water was removed and the residue was transferred into methanol. Methanol was removed and the product was dried under vacuum to afford the bis-pyridinium cyclophane (40% yield). HNMR (300 MHz, D2O), 10.11 (s, 2H), 9.37 (d, J=6.3, 2H), 8.22 (dt, J=7.8, J=1.2, 2H), 8.03 (dd, J=6.3, J=7.8, 2H), 4.99 (t, J=8.1, 4H), 2.49 (t, J=6.6, 4H), 2.15-2.17 (m, 4H), 1.38-1.75 (m, 24H). CNMR, 147.73, 145.88, 142.71, 128.04, 126.46, 102.54, 74.29, 61.82, 32.44, 28.71, 27.90, 27.83, 27.40, 25.81, 20.21.

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; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; US2010/222377; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com