Month: August 2021

Application of 54811-38-0,Some common heterocyclic compound, 54811-38-0, name is 5-Iodo-2-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Step A: Preparation of 5-iodo-2-methylbenzenemethanol Borane-methylsulfide solution (50.0 mL of a 2.0M solution in THF, lOOmmol) was added dropwise to a solution of 5-iodo-2-methyl benzoic acid (13.1g, 50 mmol) and anhydrous THF (100 mL) at 35-45 C at a rate to moderate the gas evolution. The resulting mixture was heated at 60 C for 3 h and was then cooled to 25 C and quenched by the careful, dropwise addition of methanol (50 mL) which was added at such a rate that gas evolution was moderated and the temperature was maintained below 35 C. The resulting mixture was stirred at 25 C for 2 h and was then concentrated under vacuum. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic phase was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated to provide the title compound (11.58 g) as a white solid H NMR (CDCI3) delta 7.71 (d, 1H), 7.52 (d, 1H), 6.91 (d, 1H), 4.64 (s, 2H), 2.27 (s, 3H), 1.62 (br s, 1H).

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

Reference:
Patent; E I DU PONT DE NEMOURS AND COMPANY; TAGGI, Andrew Edmund; MARCUS, Kimberly Katherine; MCCANN, Stephen Fredrick; SHAPIRO, Rafael; CHEN, Yuzhong; WO2015/157005; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 19718-49-1, 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 19718-49-1 as follows.

To a stirred solution of 4-amino-3-iodo-benzoic acid methyl ester (11.1 g, 40.0 mmol) in pyridine (80 mL) was added acetyl chloride (3.30 g, 42.0 mmol) at 0 C. under nitrogen. Stirring continued at 0 C. for 30 minutes. The ice-bath was removed, and stirring continued at room temperature for 16 hours. Pyridine was evaporated under reduced pressure. The residue was taken in ethyl acetate (300 mL). The organic phase was washed with 2 N aqueous HCl (200 mL), water (200 mL), brine (200 mL), and then dried over anhydrous Na2SO4. Removal of solvent gave 4-acetylamino-3-iodo-benzoic acid methyl ester as a white solid. Yield: 12.71 g (99%)

According to the analysis of related databases, 19718-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 199786-58-8, These common heterocyclic compound, 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, 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.

Solution of compound 3 (5.00g, 0.04mol) dissolved in dry triethylamine (100mL) was added dropwise to a suspension of compound 2 (12.52g, 0.04mol), Pd(PPh3)2Cl2 (0.63g, 0.9mmol), triphenylphosphine (0.89g, 3.4mmol), and copper(I) iodide (0.29g, 1.7mmol) in dry triethylamine (200mL) at room temperature under nitrogen. The mixture was stirred at near 80C for 24h. The mixture was cooled to room temperature and filtered to remove the insoluble salt (triethylamine hydrobromide) formed during the reaction. The filtrate was washed with ether. After concentrated, the product was purified by column chromatography [silica gel, petroleum ether: ethyl acetate (v:v)=2:1] to give 6.3g of a yellowish solid. Yield:55%; 1H NMR (600MHz, DMSO-d6): delta=7.62 (s, 1H), 7.41 (dd, J=8.2, 1.9Hz, 1H), 7.32 (d, J=8.2Hz, 1H), 7.19 (d, J=8.4Hz, 1H), 6.55 (d, J=8.5Hz, 1H), 5.58 (s, 1H), 5.42 (t, J=5.7Hz, 1H), 4.65(d, J=5.6Hz, 1H)ppm (Fig.S3). HRMS(EI,DIP); m/z calcd. for C15H12BrNO [M+H]+: 301.01, found 301 (Fig.S4).

Statistics shows that (5-Bromo-2-iodophenyl)methanol is playing an increasingly important role. we look forward to future research findings about 199786-58-8.

Reference:
Article; Guan; Jia; Zhang; Zhang; Ma; Lu; Lai; Lei; Dyes and Pigments; vol. 136; (2017); p. 873 – 880;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 69113-59-3, 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. 69113-59-3, name is 3-Iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a dry 10 mL round bottomflask, 1 (0.2 mmol), Na2S2O3 (0.21 mmol),CF3SiMe3 (0.4 mmol), CuCl/Phen(5% mol) and K3PO4 (0.3 mmol) were added sequentially andthen dissolved in 2 mL DMSO. The resulting mixture was stirred at 80 oCunder air and monitored by TLC. Purification by column chromatography on silicagave rise to 2.

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

Reference:
Article; Zhong, Wei; Liu, Xiaoming; Tetrahedron Letters; vol. 55; 35; (2014); p. 4909 – 4911;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 289039-29-8, name is 2-Chloro-5-iodobenzonitrile, 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 289039-29-8, Safety of 2-Chloro-5-iodobenzonitrile

A. 2-Chloro-5-iodo-benzaldehyde. To a 0 C. solution of 2-chloro-5-iodo-benzonitrile (10.6 g, 40.4 mmol) in toluene (100 mL) was added DiBAL-H (1.5 M in toluene; 40.4 mL, 60.6 mmol). The mixture was stirred at 0 C. for 15 min and then warmed to rt for 3 h. The mixture was poured over 1.0 M H2SO4 (10 mL), MeOH (100 mL), and ice. The mixture was stirred vigorously and then was extracted with EtOAc (200 mL). The organic layer was dried and concentrated to give the title compound (2.98 g, 31%). 1H NMR (CDCl3): 10.37 (s, 1H), 8.22 (d, J=2.2, 1H), 7.83 (dd, J=8.4, 2.2, 1H), 7.21 (d, J=8.4, 1H).

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

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

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. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-4-iodo-2-methylbenzene

General procedure: To a stirred solution of 6-bromo-3-pyridyl boronic acid (1.25 equiv, 847 mg, 4.20 mmol) in 1,4-dioxane (30 mL) under nitrogen were added 5-bromo-2-iodotoluene (1 g, 3.36 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.05 equiv, 195 mg, 0.17 mmol). After 5 min of stirring, aqueous Na2CO3 (2.5 equiv, 892 mg, 8.42 mmol) in 5 mL of water was added. Then the mixture was heated to 80 C until the starting material was consumed (TLC). After cooling down to room temperature, the mixture was filtered on Celite and washed with CH2Cl2. The aqueous layer was extracted with EtOAc (2×50 mL). Combined organic layers were washed with saturated aqueous solution of NaCl (50 mL), and dried over MgSO4. Solvent was removed in vacuo and crude product was purified by column chromatography, with 99:1 cyclohexane/EtOAc affording 3c as a white solid (520 mg, 47%).

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 202865-85-8.

Reference:
Article; Perato, Serge; Voisin-Chiret, Anne Sophie; Sopkova-De Oliveira Santos, Jana; Legay, Remi; Oulyadi, Hassan; Rault, Sylvain; Tetrahedron; vol. 68; 7; (2012); p. 1910 – 1917;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 364-77-2 as follows. Quality Control of 2-Iodo-5-fluoronitrobenzene

Into a round bottom flask was added 3-ethynyl-2-fluoropyridine (0.3 g, 0.002 mol), 4- fluoro-l-iodo-2-nitrobenzene (0.675 g, 0.00253 mol), bis(triphenylphosphine)palladium(II) chloride (0.09 g, 0.1 mmol), copper(I) iodide (0.04 g, 0.2 mmol), and triethylamine (0.52 mL, 3.7 mmol) in N,N-dimethylformamide (4 mL). The reaction was stirred at room temperature for 2 hours. The reaction was extracted with ethyl acetate, and the combined organic extracts were washed with brine (3x), dried over MgSO4, and purified by column chromatography on silica gel (10% ethyl acetate 90% hexanes), to give 0.443 g of product. 1H nuMR (400 MHz, CDCl3): delta 8.44-8.50 (m, IH), 7.99-8.02 (m, IH), 7.79-7.90 (m, IH), 7.78-7.82 (m, IH), 7.37- 7.42 (m, IH), 7.23-7.29 (m, IH). MS [M+H]=261.0.

According to the analysis of related databases, 364-77-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; WO2007/38215; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 58313-23-8,Some common heterocyclic compound, 58313-23-8, name is Ethyl-3-iodobenzoate, molecular formula is C9H9IO2, 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.

A -45 C. solution of ethyl 3-iodobenzoate (2.434 g, 8.8 mmol) in 40 mL THF was treated with i-PrMgCl (4.8 mL, 9.6 mmol, 2 M/ether). After 1 h, allyl bromide (1.6 mL, 18.9 mmol) was added followed by CuCN (79 mg, 0.88 mmol). The reaction was stirred for 1 h and then was quenched by addition of 50 mL saturated NH4Cl solution. Water (30 mL) was added and the resulting mixture was extracted with ethyl acetate (3*50 mL). The combined ethyl acetate solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (5% ethyl acetate/hexanes?10%) gave compound 7 (1.145 g, 68%).

The synthetic route of 58313-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; US2009/239869; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 216393-67-8, A common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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.

To a mixture of 3-ethynylpyridine (1.13 g, 11 mmol) and 2-fluoro^-chloro-6-iodoaniline (2.71 g, 10 mmol) in triethylamine (100 mL) is added PdCI2(PPh3)2 (175 mg, 0.25 mmol) and CuI (95 mg, 0.50 mmol) and the mixture is refluxed for 1 h. The solvent is removed in vacuo and the residue is purified by silica gel flash chromatography (dichloromethane- methanol, 1 :0 to 24:1 ) to give 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine. MS (ESI) m/z 247 (M+H)+.

The synthetic route of 216393-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/156462; (2009); A2;,
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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrIO2

General procedure: 500mL round-bottom flask reactor, methyl 5-bromo-2-iodo benzoate (25.0g, 73mmol) in 4-dibenzofuran boronic acid(18.7g, 88mmol), tetrakis (triphenylphosphine) palladium (1.7g, 0.15mmol), potassium carbonate (20.2 g,Put 146.7mmol) were placed 125 mL toluene, tetrahydrofuran, 125mL, water 50 mL. The temperature of the reactor 80 road winsOn and stirred 10 hours. When the reaction is complete cool down the temperature of the reactor to room temperature, extracted with ethyl acetate and the organicAnd separating the base layer. The organic layer was obtained an intermediate a-1 (75.0g, 60.1%) and, after concentration under reduced pressure, separated by column chromatography. Synthesis Example 1- (1) in the 4-dibenzofuran boronic acid, except that instead of the and is, using the same method to give the (8.2g, 68.6%) .

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; SFC CO., LTD.; CHA, SUN OK; JONG, KYONG SEOK; SONG, JOO MIN; LEE, YU RIM; PARK, SANG WOO; KIM, HUI DAE; PARK, SEOK BAE; (76 pag.)KR2016/13678; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com