Month: February 2021

These common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-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

General procedure: To a solution of phenol 3 (0.45 mmol), aryl iodide 2 (0.45 mmol), ferrocenyl allene 1 (0.3 mmol) and Cs2CO3 (0.9 mmol) in MeCN (2.0 mL)was added Pd(PPh3)4 (0.015 mmol) under a N2 atmosphere. The resulting mixture was heated at 80 ¡ãC for 2 h. After completion of thereaction, the mixture was cooled to room temperature. The solvent was removed under vacuum, and the resulting residue was purified on a silica gel column (PE/EtOAc, 10:1) to provide the corresponding ferrocene-containing allylic ester product

The synthetic route of 1,3-Dichloro-5-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Xin-Xing; Wang, Chenjun; Zhao, Wanrong; Zhao, Haiying; Chen, Shufeng; Synthesis; vol. 50; 20; (2018); p. 4097 – 4103;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 391211-97-5,Some common heterocyclic compound, 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, molecular formula is C13H7F3INO2, 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.

Example 4. Preparation of N-((R)-2.3-dihydroxypropoxyV3.4-difluoro-2-(2-fluoro-4-iodo-phenylanriotainoV benzamide (Compound ) To a stirring solution of 3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzoic acid (9) (120 g, 0.30 mol) in a mixture of 1 mL N,N-dimethylformamide and 1000 mL toluene was added thionyl chloride (55 g, 0.462 mol). The mixture was heated to 50-65 C and stirred for 2 hours or until reaction completion as determined by HPLC (Conditions E). The final reaction mixture was then cooled and concentrated under reduced pressure to a slurry keeping the temperature below 35C. Toluene (600 mL) was added to dissolve the slurry and vacuum distillation was repeated. Additional toluene (600 mL) was added to the slurry dissolving all solids and the solution was then cooled to 5 -10C. The solution was then treated with O-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}hydroxylamine (6) (63 g, 0.43 mol) solution in 207 mL toluene followed by potassium carbonate (65 g) and water (200 mL), stirred for at least 2 hours at 20- 25C. The stirring was stopped to allow phase separation and the bottom phase was discarded. The remaining organic layer was treated with hydrochloric acid solution (7.4%, 240 mL) until pH was less than 1 and stirred for 2 hours. The final reaction mixture was slightly concentrated under vacuum collecting about 100 mL distillate and the resulting organic solution was cooled to 5C to crystallize the product and filtered. The filter cake was washed with toluene (1000 mL) followed by water (100 mL) and the wet cake (crude product Compound I) was charged back to the flask. Toluene (100 mL), ethanol (100 mL) and water (100 mL) are then added, stirred at 30-35C for about 15 min, and the bottom aqueous phase was discarded. Water (200 mL) was then added to the organic solution and the mixture was stirred at about 3O C to allow for crystallization. The stirring was continued for 2 hours after product crystallized, then it was further cooled to about 0C and stirred for at least 2 hours. The slurry was filtered and wet cake was dried under reduced pressure at 55-85C to yield the final product N-((R)-2,3-dihydroxypropoxy)-3,4- difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide (Compound I) product. Overall chemical yield was 86 g, 58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/134469; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 811842-30-5, The chemical industry reduces the impact on the environment during synthesis 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, I believe this compound will play a more active role in future production and life.

Add QD105 (200g, 0.78mmol), 2-bromo-4-iodo-1-methylbenzene (457mg, 1.54mmol), potassium carbonate(323mg, 2.34mmol) and valine (18mg, 0.16mmol) to the eggplant In the flask, dimethyl sulfoxide was added, andthe reaction solution was deoxidized. Copper iodide (16 mg, 0.08 mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 256 mg.

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-Bromo-1-fluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 199850-56-1, 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. 199850-56-1 name is Methyl 2-amino-4-chloro-5-iodobenzoate, 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.

A solution ofmethyl2-amino-4-chloro-5-iodobenzoate (3.4 g, 10.9 mmol) and imidoformamide (3.4 g, 32.7 mmol) in 2-methoxyethanol (15 mL) was stirred at 125C for 7 h. The reaction mixture was allowedto cool to rt and the residue suspended in water. The solid was collected by filtration,5 washed with water and dried under vacuum (50 C) to give 3.2 g of the title compound(96%). MS: m/z: 307 [M+H+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-4-chloro-5-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; EIDAM, Patrick, M.; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; SINGHAUS, Robert, R., Jr.; SHAH, Ami, Lakdawala; WANG, Gren; WO2013/25958; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 791642-68-7, 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. 791642-68-7 name is 4-Bromo-1-iodo-2-methoxybenzene, 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.

5-Bromo-2-lodoanisole (4g, 14.09 mmol), Boc-Piperazine (2.5 g, 13.42 mmol), Pd2(dba)3 (368 mg, 0.4 mmol), XantPhos (699 mg, 1.21 mmol), Sodium t-butoxide (3.8 g, 40.27 mmol) were combined in toluene (36 mL), heated to 60 C for 3h. The reaction was diluted with water, extracted with EtOAc, dried (MgSO4), filtered and concentrated. The crude product was purified by flash silica chromatography (10% MeOH in DCM). Pure fractions were evaporated to dryness to give tert-butyl 4-(4-bromo-2- methoxyphenyl)piperazine-1-carboxylate]

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

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13194-68-8,Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

Preparation 1 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid To a stirred solution comprised of 1.88 g (0.00791 mol) of 2-amino-5-iodotoluene in 10 mL of tetrahydrofuran at -78 C. was added 6 mL (0.012 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 10 minutes, after which time a solution of 1.00 g (0.00392 mol) of 5-bromo-2,3,4-trifluorobenzoic acid in 15 mL of tetrahydrofuran was added. The cold bath was subsequently removed, and the reaction mixture stirred for 18 hours. The mixture was concentrated, and the concentrate was treated with 100 mL of dilute (10%) aqueous hydrochloric acid. The resulting suspension was extracted with ether (2*150 mL), and the combined organic extractions were dried (MgSO4) and concentrated in vacuo to give an orange solid. The solid was triturated with boiling dichloromethane, cooled to ambient temperature, and collected by filtration. The solid was rinsed with dichloromethane, and dried in the vacuum-oven (80 C.) to afford 1.39 g (76%) of a yellow-green powder; mp 259.5-262 C.; 1H NMR (400 MD, DMSO): delta9.03 (s, 1H), 7.99 (dd, 1H, J=7.5, 1.9 Hz), 7.57 (dd, 1H, J=1.5 Hz), 7.42 (dd, 1H, J=8.4, 1.9 Hz), 6.70 (dd, 1H, J=8.4, 6.0 Hz), 2.24 (s, 3H); 19F NMR (376 MHz, DMSO): delta-123.40 to -123.47 (m); -139.00 to -139.14 (m); IR (KBr) 1667 (C=O stretch)cm-1; MS (CI) M+1=469. Anal. Calcd/found for C14H9BrF2INO2: C, 35.93/36.15; H. 1.94/1.91; N, 2.99/2.70; Br, 17.07/16.40; F, 8.12/8.46; I, 27.11/26.05.

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-2-methylaniline, its application will become more common.

Reference:
Patent; Barrett, Stephen Douglas; Biwersi, Cathlin Marie; Chen, Michael Huai Gu; Kaufman, Michael David; Tecle, Haile; Warmus, Joseph Scott; US2004/54172; (2004); A1;,
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. 68507-19-7, name is 3-Iodo-4-methoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7IO3

[00164] To 26.9 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.43 ml (3 mmol) triethylamine, 0.35 ml (2.4 mmol) pinacolborane and 277 mg (1.0 mmol) 3-iodo-4-methoxybenzoic acid. The reaction solution was stirred at room temp. to ensure that all the phenolic groups had reacted with pinacolborane and the hydrogen evolved was flushed out of the reaction tube with argon. The reaction solution was warmed to 80 C. with stirring in an oil bath for 8 h. An aliquot (0.3 ml) was removed from the reaction solution, extracted into ethyl acetate, washed with dilute sulphuric acid and then several times with water and analysed by gc (fid detector, SGE HT5 capillary column). There was only one peak in the gc at retention time longer than that for 3-iodo-4-methoxybenzoic acid and that was confirmed by gc/ms to be due to the desired arylboronic acid pinacol ester.

According to the analysis of related databases, 68507-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-Iodo-4-methylbenzoic acid

To a stirring solution of 3-iodo-4-methylbenzoic acid (60 g, 0.22 mol, 1 eq) in degassed DMF (1400 niL, 23.3 vol.) was charged 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-l,3,2- dioxaborolane (81.4 g, 0.32 mol, 1.4 eq) followed by potassium acetate (112 g, 1.14 mole, 5eq) and [1,1 ‘-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (18.7 g, 0.02 mole, 0. leq). The resulting mixture was placed under a nitrogen atmosphere and was heated to 80 0C with the exclusion of light overnight. The mixture was then concentrated under high vacuum and the residue partitioned between EtOAc and 2M HCl. The mixture was then filtered and the layers separated. The aqueous phase was re-extracted with EtOAc. The combined organics were then washed with brine, dried and evaporated to yield a brown solid that was applied to a silica plug then eluted with 2:1 cyclohexane : ethyl acetate. Fractions were then combined and evaporated to yield a brown foam that was triturated with cyclohexane, collected by filtration then dried in vacuo to yield 4-methyl-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid, delta (CDCl3) 8.50-8.49 (IH, d), 8.04-8.02 (IH, dd), 7.27-7.25 (IH, d), 2.61 (3H, s), 1.36 (12H, s).

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/147104; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, 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 199786-58-8, name: (5-Bromo-2-iodophenyl)methanol

(5-Bromo-2-iodophenyl)methanol (8c) (106 mg, 0.34 mmol), Pd(PPh3)2Cl2 (7.0 mg, 0.01 mmol) and Cul (1.2 mg, 6.3 mupiiotaomicron) were added to a flame-dried Schlenk flask. The flask was evacuated and refilled with an N2/H2-mixture (3 :2) three times. Dry THF (3 mL) and dry NEt3 (71 mu, 0.51 mmol) were bubbled through with an N2/H2 mixture (3 :2) for 10 minutes and subsequently added to the mixture. After this time, 2-ethynylaniline (0.060 mL, 0.58 mmol) was added and the mixture was stirred for 16 hours under an N2/H2-atmosphere. The reaction mixture was diluted with CH2C12 (5 mL) and the organic layer was washed with H20 (5 mL). The water layer was then back-extracted with CH2C12 (2 x 5 mL). The combined organic layers were washed with H20 (15 mL) and brine (20 mL). Next, the organic layer was dried over MgS04 and concentrated in vacuo. The crude product was purified by gradient column chromatography (EtOAc/-heptane, 1 :6 to 1 :2) to obtain 9c as a yellow solid (102 mg, 100%). RF = 0.40 (EtOAc/-heptane, 1 :2). 1H-NMR (300 MHz, CD3OD) delta: 7.68-7,67 (m, 1H), 7.43-7.42 (m, 2H), 7.28 (ddd, J = 7.7, 1.5, 0.4 Hz, 1H), 7.12 (ddd, J = 7.3, 6.6, 1.6 Hz, 1H) 6.79-6.76 (m, 1H) 6.64 (td, J = 7.7, 1.1 Hz, 1H), 4.80 (d, J = 0.6 Hz, 2H). 13C-NMR (75 MHz, CD3OD) delta: 148.6, 144.2, 132.4, 131.0, 129.4, 129.2, 129.1, 121.4, 120.0, 1 16.5, 1 13.8, 106.5, 91.6, 89.8, 61.3. FT- IR max film (cm”1): 3360, 2923, 2850, 2362, 2202, 1610, 1489, 1450, 815, 750. HRMS (ESI+) m/z calcd for Ci5Hii3brNO [M+H]+ 302.0181, found 302.0169.

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-iodophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; STICHTING KATHOLIEKE UNIVERSITEIT; SYNAFFIX B.V.; DEBETS, Marjoke Froukje; RUTJES, Floris Petrus Johannes Theodorus; VAN HEST, Jan Cornelis Maria; VAN DELFT, Floris Louis; VAN BERKEL, Sander Sebastiaan; WO2014/189370; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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. Product Details of 103440-52-4

General procedure: A dry, N2 flushed 25 mL round-bottomed flask, equipped with a magnetic stirring bar, was charged with aryl iodide 3 (1 mmol) in anhydrous THF (5 mL), and cooled to -40 C. i-PrMgCl (2 M in THF, 2 mmol) was slowly added. After 0.5 h, CuCN¡¤2LiCl (premixed CuCN and 1 M LiCl in THF) (0.1 mmol) was added. After 5 min, at the same temperature, 2-chloro-3-iodo-propene (2 mmol) was added and the reaction mixture allowed to warm to rt. The reaction mixture was quenched with sat. NH4Cl (20 mL) and extracted with MTBE (2 ¡Á 20 mL). The combined organic fractions were washed with brine (10 mL), then dried over Na2SO4, and concentrated in vacuo. The crude product was used in the next step after a silica plug treatment or without further purification.

The synthetic route of Methyl 2-Iodo-5-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Linghu, Xin; McLaughlin, Mark; Chen, Cheng-Yi; Reamer, Robert A.; Dimichele, Lisa; Davies, Ian W.; Tetrahedron Letters; vol. 53; 13; (2012); p. 1550 – 1552;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com