Month: April 2021

Synthetic Route of 29289-13-2, A common heterocyclic compound, 29289-13-2, name is 2-Iodo-4-methylaniline, molecular formula is C7H8IN, 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.

General procedure: A mixture of 2-iodoaniline 1 (0.5 mmol) and Pd(OAc)2 (5.6 mg, 0.025 mmol, 5.0 mol%) in CH3CN (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature. Followed by the addition of ethyl acrylate 2a (100 mg, 1.0 mmol, 2.0 equiv) and triethylamine (101 mg, 1.0 mmol, 2.0 equiv), the mixture was stirred at 100 C until the reaction was finished. Then the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1 to 2:1) afforded the corresponding alkenylanilines 3.

The synthetic route of 29289-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xia; Zhou, Xiao-Yu; Wang, Liang-Guang; Synthetic Communications; vol. 47; 22; (2017); p. 2096 – 2102;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Iodo-3-(trifluoromethyl)benzene

General procedure: In an oven-dried Schlenk tube iodoarenes 1 (0.25 mmol), arylboroicacids 2 (0.5 mmol), PdO/GO nano catalyst (5 mol%),K2CO3 (0.5 mmol) and solvent (DMSO) (1.0 mL) wereadded. The resulting reaction mixture was stirred at 120 Cfor 5-30 min. The progress of the reaction was monitoredby TLC. After completion of reaction, the reaction mixturewas allowed to cool to room temperature, then diluted with(approximately 10 mL) ethyl acetate and NH4Cl solution(approximately 10mL)was added followed by extractionwithethyl acetate. The organic layers were dried with Na2SO4 andconcentrated in reduced vacuum. Purification of the residue bysilica gel column chromatography using distilled petroleumether/ethyl acetate as the eluent furnished the biphenyls.

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 401-81-0.

Reference:
Article; Lakshminarayana, Bhairi; Mahendar, Lodi; Chakraborty, Jhonti; Satyanarayana, Gedu; Subrahmanyam, Ch; Journal of Chemical Sciences; vol. 130; 5; (2018);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

Intermediate XI A solution of isopropyl magnesium chloride (100 mL, 2.0M in Ethyl Ether) was added to a solution of 2-chloro-4-fluoro-1-iodobenzene (25 g, 97.5 mmol) in 300 mL THF chilled in an ice bath. The solution was then stirred at RT overnight. The solution was chilled in a CO2/acetone bath and trimethyl borate was added (23 mL, 200 mmol). The solution was warmed to RT and stirred for 6 h. The suspension was partitioned between water and ethyl ether (emulsion). The phases were separated and the organic phase concentrated. The residue was treated with 200 mL 2N HCl and stirred overnight. The suspension was then extracted with ethyl ether (2*) and the combined organics washed with brine, dried over MgSO4, filtered and concentrated to give 13.3 g solid. The crude solid was suspended in hexanes, filtered and washed 2* (hexanes) to give 2-chloro-4-fluoro-phenylboronic acid. LC 1: 1.65 min.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doherty, James B.; Stelmach, John E.; Chen, Meng-Hsin; Liu, Luping; Hunt, Julianne A.; Ruzck, Rowena D.; Goulet, Joung L.; Wisnoski, David D.; Natarajan, Swaminathan Ravi; Rupprecht, Kathleen M.; Bao, Jianming; Miao, Shouwu; Hong, Xingfang; Sinclair, Peter J.; Kallashi, Florida; US2003/92712; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9IO2

Compound 1 was mixed with with aryliodide 2c (132.0 mg, 0.50 mmol), ortho-bromoacetophenone 1a (109.4 mg, 0.55 mmol), Pd(OAc)2 (2.2 mg, 2 molpercent), xantphos (11.6 mg, 4 molpercent), tBuOK (72.9 mg, 0.65 mmol), and dry toluene (4 mL)at 80 ¡ãC for 45 min. Silica-gel column chromatography (20g, petroleum ether/ethyl acetate, 85:15 to 80:20) furnished the title compound 3ac (155 mg, 92percent) as yellow solid, recrystallized the solid with dichloromethane/hexane, mp 74?76 ¡ãC [TLCc ontrol (petroleum ether/ethyl acetate 90:10), Rf(1a)0.55, Rf(2c)0.45, and Rf(3ac) 0.20, UV detection]. IR (MIR-ATR, 4000?600 cm1): numax2956, 2923,2852, 1697, 1587, 1512, 1463, 1422, 1259, 1154, 1140, 1025, 791, 757, 678 cm1. 1HNMR (CDCl3, 400 MHz): d7.57 (d, 1H, J7.8 Hz, Ar-H), 7.35?7.15 (m, 3H,Ar-H), 6.78 (d, 1H, J8.7 Hz, Ar-H), 6.76 (dd, 1H, J8.7 and 1.9 Hz, Ar-H),6.74 (d, 1H. J1.9 Hz, Ar-H), 4.15 (s, 2H, ArCOCH2), 3.83 (s, 3H, ArOCH3),3.82 (s, 3H, ArOCH3) ppm. 13C NMR (CDCl3, 100 MHz): 201.8 (s, Ar-C=O),148.9 (s, Ar-C), 148.1 (s, Ar-C), 141.4 (s, Ar-C), 133.5 (d, Ar-CH), 131.4 (d, Ar-CH),128.6 (d, Ar-CH), 127.2 (d, Ar-CH), 125.8 (s, Ar-C), 121.9 (d, Ar-CH), 118.6(s, Ar-C), 112.7 (d, Ar-CH), 111.2 (d, Ar-CH), 55.8 (q, 2C, 2ArOCH3), 49.0 (t, Ar-COCH2) ppm. HR-MS (ESI) m=z calculated for [C16H7916 BrO3][MH]:335.0277; found 335.0294. [C16H8116 BrO3][MH]: 337.0259; found 337.0274.

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:
Article; Krishna, Jonnada; Reddy, Alavala Gopi Krishna; Satyanarayana, Gedu; Synthetic Communications; vol. 44; 14; (2014); p. 2103 – 2111;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 31599-61-8,Some common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, molecular formula is C8H9I, 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.

1.0 mmol of 3,4-dimethyliodobenzene,1.2 mmol sodium azide,0.15 mmol DBUAnd 0.1mmol of copper acetate were sequentially added to a reaction flask equipped with 3mL of dimethyl sulfoxide,The reaction mixture was stirred at 95 C for 2.5 h,TLC was followed until the reaction was complete,A few drops of aqueous ammonia were added to the reaction mixture,Then extracted with ethyl acetate (10 mL ¡Á 3),Then washed once with saturated saline,dry,Suction filtration,Remove the solvent,Purification by column chromatography gave the desired product,Yield 90%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1,2-dimethylbenzene, its application will become more common.

Reference:
Patent; Henan Normal University; Jiang Yuqin; Zhao Yaru; Ma Suhao; Li Xingfeng; Dong Wenpei; Xu Guiqing; (10 pag.)CN106588693; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 148836-41-3, name is 1-Bromo-4-chloro-2-iodobenzene, 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 148836-41-3, COA of Formula: C6H3BrClI

Step 2. Ethyl 4-(2-(5-(2-bromo-5-chlorophenyl)pyridin-2-yl)-3-cvclopropylpropanamido) benzoate (9-B) To a round bottom flask was added 9-A from step 1 , l-bromo-4-chloro-2- iodobenzene (66.0 mg, 0.208 mmol), K2CO3 (43.1 mg, 0.312 mmol) and [l ,l’-bis(diphenyl phos- phino)ferrocene]dichloropalladium (15.22 mg, 0.021 mmol) at 13C. The reaction mixture was stirred at 50C for 18 h. The mixture was filtered and concentrated. The residue was purified by preparative TLC (Si02, PE_EtOAc=2: l) to give the title compound. 1H NMR (CDCI3, 400MHz): delta 10.21 (s, 1 H), 8.71 (d, J=2.0 Hz, 1 H), 8.06 (d, J=8.8 Hz, 2 H), 7.76 – 7.88 (m, 2 H), 7.71 (d, J=8.6 Hz, 2 H), 7.43 – 7.50 (m, 2 H), 7.33 (d, J=8.2 Hz, 1 H), 4.41 (q, J=7.1 Hz, 2 H), 3.98 (t, J=7.5 Hz, 1 H), 2.03 – 2.20 (m, 2 H), 1.44 (t, J=7.1 Hz, 2 H), 0.69 – 0.81 (m, 1 H), 0.42 – 0.56 (m, 2 H), 0.19 (dd, J=9.2, 4.5 Hz, 1 H), -0.02 – 0.06 (m, 1 H). MS (ESI) m/z 529.2 (M+H).

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; MERCK SHARP & DOHME CORP.; LIU, Weiguo; EDMONDSON, Scott, D.; GUO, Zhuyan; MERTZ, Eric; OGAWA, Anthony, K.; SO, Sung-Sau; SUN, Wanying; BROCKUNIER, Linda, L.; ALI, Amjad; KUANG, Rongze; WU, Heping; WO2015/183709; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, A new synthetic method of this compound is introduced below., Product Details of 2043-57-4

1-Methylimidazole (4.32 g, 0.52 mol) was partially dissolved in reagent-grade toluene (50 ml) in a large round-bottomed flask and stirred vigorously. 1,1,1,2,2,3,3,4,4,5,5,6, 6-Tridecafluoro-8-iodooctane (26 g, 0.053 mol) was added, and the mixture was heated under reflux at 110 degrees C for 24 hours. The solvent was removed under vacuum giving l-methyl-3- (3,3,4,4,5,5,6,6,7,7,8,8,8- tridecafluorooctyl) imidazolium iodide (30.5 g) as a waxy solid. Potassium 1,1,2,2- tetrafluoroethanesulfonate (TFES-K, 12 g) was added to reagent grade acetone (100 ml) in a separate round- bottomed flask, and this solution was carefully added to the l-methyl-3- (3,3,4,4,5,5, 6, 6,7,7, 8, 8, 8- tridecafluorooctyl) imidazolium iodide which had been dissolved in acetone (50 ml) . The reaction mixture was heated under reflux for approximately 16 hours. The reaction mixture was then filtered using a large frit glass funnel to remove the white KI precipitate formed, and the filtrate was placed on a rotary evaporator for 4 hours to remove the acetone. The oily liquid was then filtered a second time to yield the product, as shown by proton NMR.

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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/32959; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 31928-46-8, 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. 31928-46-8 name is 2-Bromo-1-chloro-4-iodobenzene, 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.

To a solution of 2-Bromo-l-chloro-4-iodo-benzene (1 1.8 g, 37.2 mmol) and but-3-yn-l-ol (2.9 g, 40.9 mmol) in dried triethylamine (50 mL) was added copper (I) iodide (1.4 g, 7.4 mmol) and then bis(triphentlphosphine)palladium (II) dichloride (3.0 g, 3.7 mmol). The mixture was degassed by nitrogen for 3 times and then kept stirred at 90 C for 5 h. The resulting mixture was diluted with EtOAc and then filtered. The filtrate was concentrated under reduced pressure and purified via flash-chromatography on silica gel (10 % EtOAc in petroleum ether) to give 4-(3-Bromo-4-chloro-phenyl)-but-3-yn-l-ol (7.4 g, yield 77 %) as white solid. MS ESI calc’d. For Ci0H8BrClO [M + H]+ 261, found 261.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-chloro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ANDRESEN, Brian, M.; ANTHONY, Neville, J.; MILLER, Thomas, A.; WO2014/74422; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 127654-70-0,Some common heterocyclic compound, 127654-70-0, name is 1-Chloro-3-fluoro-2-iodobenzene, molecular formula is C6H3ClFI, 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 a solution of 1-chloro-3-fluoro-2-iodobenzene (0.335 g, 1.30 mmol) in tetrahydrofuran (1.5 mL), isopropylmagnesium chloride lithium chloride (0.878 ml, 1.3 M solution) was added at -10 C and the resulting mixture was stirred for 1 hour before a solution of 3 -(8-(bis(4-methoxybenzyl)amino)-2-formyl-5 -(pyrimidin-4-yl)-[1,2,4jtriazolo[1,5-ajpyrazin-6-yl)benzonitrile (0.190 g, 0.326 mmol) (from Example49 step 8) in THF (1.5 mL) was added at -10 C. The reaction mixture was stirred for60 minutes, then quenched with ammonium chloride solution (3 mL), and extractedwith dichloromethane. The combined organic layers were concentrated undervacuum. The cmde material was directly purified by a silica gel column to afford thedesired product (147 mg, 63%) as a racemic mixture. LC-MS calculated forC39H31C1FN803 (M+H): m/z = 713.2; found 713.3.

The synthetic route of 127654-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6828-35-9, name is 5-Chloro-2-iodoaniline, 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

General procedure: A mixture of o-iodoaniline (0.5 mmol, 1 equiv), arylacetic acid (0.6 mmol), elemental sulfur (1.5mmol), Cu(OAc)2¡¤H2O (20 mmol%), and NaOH (1.0 mmol) in DMSO (3 mL) was put into a sealed pressure vessel (25 mL) containing a magnetic stirring bar. The tube was purged with nitrogen three times, and then capped and stirred in a preheated oil bath at 130 C for 24 h. The reaction mixture then cooled to room temperature and extracted with ethyl acetate (3×10 mL), the organic layer was washed with saturated NaCl (2×10 mL), dried over anhydrous Na2SO4, evaporated under vacumm and then purified by silica gel column chromatography by using petroleum ether and ethyl acetate (PE:EA=200:1) as eluent.

The synthetic route of 6828-35-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xin; Li, Xiaotong; Hu, Renhe; Yang, Zhao; Gu, Ren; Ding, Sai; Li, Pengyi; Han, Shiqing; Synlett; vol. 29; 2; (2018); p. 219 – 224;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com