Month: August 2021

Electric Literature of 1829-28-3, A common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

[00319] 25.5 mg of PdCl2[dppf].CH2Cl2 was placed in a reaction tube under nitrogen and added 4 ml dioxane and 0.45 ml triethylamine. The mixture was heated at 80 C. for 23 h to give a brownish solution. To this solution was then added 286 mg (1.04 mmol) of ethyl 2-iodobenzoate and 0.23 ml (1.6 mmol) pinacolborane. The reaction mixture was heated with stirring to 80 C. for 16.5 h and then analysed by gc and the products identified by gc/ms. The gc solutions were prepared by washing an aliquot of the reaction solution dissolved in ethyl acetate with water and dried. The reaction was finished, the desired product peak in the gc had an area of 84percent with the only other significant peak being that due to the dehalogenation product, ethyl benzoate (14percent).

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; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 14452-30-3,Some common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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 cooled (-40 C) stirred solution of TiC4 (11 mL of a 1. OM sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5. 5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min iodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an additional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnisium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil.

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); 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. 4387-36-4, name is 2-Iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Iodobenzonitrile

2-iodobenzonitrile (1.5mmol) was dissolved in a 3:2 mixture of Net3/THF (10 mL) and degassed for 30 min at room temperature. After adding of PdCl2(PPh3)2 (0.2 mol percent) and CuI (0.2mol percent), alkyne (1.8mmol) was added dropwise to the reaction suspension. Subsequently the reaction mixture was stirred at room temperature until completion was indicated by TLC. After the completion of the reaction, the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1a (yield: 78percent), 1k-1s (in 77?85percent yield).

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 4387-36-4.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16932-44-8, 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 16932-44-8 as follows.

0.2 mmol of potassium carbonate, 0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol, 18-crown-6-ether 0.1mmol,1,3-dimethoxy-2-iodobenzene 0.1 mmol,1-phenyl-1-pentyne 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube, Repeatedly filled with nitrogen 10 times, stirred at room temperature for 15min, added 0.5mmol of water,Then placed in a reaction dish at 100 C for 16h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 8.9mg of the target product Color oil, 32% yield.

According to the analysis of related databases, 16932-44-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (12 pag.)CN110256184; (2019); A;,
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. 13194-68-8, name is 4-Iodo-2-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Iodo-2-methylaniline

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): delta 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): delta 69.87, 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.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US6696440; (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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, A new synthetic method of this compound is introduced below., name: 1,2-Difluoro-4-iodobenzene

In a glassware flask equipped with a condenser and a magnetic stirrer, were put 85.7 g (357 mmol) of 3,4-difluoroiodobenzene, 43.2 g (680 mmol) of copper powder, and 86 g of N-methylpyrrolidinone (NMP). The mixture was stirred under nitrogen atmosphere on an oil bath at 190 C for 5 h. After cooling to room temperature, the reaction mixture was mixed with 300 mL of tert-butyl methyl ether and filtered in order to remove copper and its salt. The filtrate was washed with water (300 mL x 3) and then with saturated aqueous sodium chloride solution (300 mL x 1), and dried with magnesium sulfate and filtered. The filtrate was evaporated and the resulting residue was column-chromatographed using hexane as an eluent to give a white solid (35 g, 87% yield) of product 4. The spectral data agreed with those of the authentic sample: 19F NMR (CDCl3) (with 1H decoupling) delta -136.88 (d, J = 21 Hz, 2F), -139.64 ppm (d, J = 21 Hz, 2F); 1H NMR (CDCl3) delta 7.25 (m, 4H), 7.34 ppm (m, 2H).

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Umemoto; Zhou, Xiaocong; Li, Yuanqiang; Journal of Fluorine Chemistry; vol. 226; (2019);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 128140-82-9,Some common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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 110; Preparation of 1-(difluoromethoxy)-4-ethynylbenzene; A solution of 1-(difluoromethoxy)-4-iodobenzene (12.7 g, 50 mmol) in triethylamine is treated with tetrakis(triphenylphosphine)palladium (4.0 g, 3.5 mmol), copper iodide (925 mg, 4.85 mmol), and a solution of ethynyl(trimethyl)silane (6.9 mL, 50 mmol) in acetonitrile at room temperature, stirred for 1 h at 60 C. and concentrated in vacuo. The resultant residue was dissolved in Et2O and filtered. The filtrate was concentrated and the concentrate was purified by chromatography (silica gel, EtOAc/hexane: 5/95) to give {[4-(difluoromethoxy)phenyl]ethynyl}(trimethyl)silane (11.5 g, 96%) as an oil. A solution of {[4-(difluoromethoxy)phenyl]ethynyl}(trimethyl)silane (10.0 g, 41.7 mmol) in MeOH/CH2Cl2 (1/1) was treated with cesium carbonate (16.3 g, 50 mmol) at room temperature, stirred for 1.5 h, diluted with CH2Cl2 and filtered through a pad of silica gel. The filtrate was concentrated to dryness to give the title compound (6.8 g, 97%) as an oil. MS (+) EI: 168.

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

Reference:
Patent; Wyeth; US2007/4730; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 340825-13-0, 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. 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Alternative Procedure: A solution of 6-iodo-3,4-dihydronaphthalen-1(2H)-one (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.

The synthetic route of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 3058-39-7, These common heterocyclic compound, 3058-39-7, name is 4-Iodobenzonitrile, 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 50mL round-bottomed flask equipped with a gas inlet tube, a reflux condenser, and a magnetic stirring bar was charged with MCM-41-S-PdCl2 (173mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa (7.5 mmol). The flask was flushed with carbon monoxide. DMF (5 mL) was added by syringe and a slow stream of CO was passed into the suspension. The mixture was vigorously stirred at 100?110°C for 4?24h, cooled to room temperature, and diluted with diethyl ether (50 mL). The palladium catalyst was separated from the mixture by filtration, washed with distilled water (2×10 mL), ethanol (2×10 mL) and ether (2×10 mL) and reused in the next run. The ethereal solution was washed with water (3×20mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane?ethyl acetate=10:1). (0008) All formylation products were characterized by comparison of their spectra and physical data with authentic samples. IR spectra were determined on a Perkin-Elmer 683 instrument. 1H NMR (400MHz) and 13C NMR (100MHz) spectra were recorded on a Bruker Avance 400MHz spectrometer with TMS as an internal standard and CDCl3 as solvent.

The synthetic route of 3058-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hao, Wenyan; Ding, Guodong; Cai, Mingzhong; Catalysis Communications; vol. 51; (2014); p. 53 – 57;,
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. 1878-69-9, name is 2-(3-Iodophenyl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(3-Iodophenyl)acetic acid

Add 1,1-carbonyldimidazole (0.72 g, 4.40 mmol) to a solution of 3-iodo-phenylacetic acid (1.20 g, 4.6 mmol) in 40 mL of N,N-dimethylacetamide, followed by N,N-diisopropylethylamine (0.79 mL, 4.40 mmol). Stir the mixture at room temperature for 2 h, add 4-cyano-benzoic acid hydrazide (0.64 g (4.0 mmol) and heat the mixture to 60 C for 2 h. Cool the mixture to room temperature and dilute with H20 causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with H20 and diethyl ether dry. Collect any further material that may crystallize from the filtrate. Extract the filtrate with CH2C12 and concentrate the combined organic phase provide a clear liquid. Dilute this mixture with H20 resulting in a third crop of material to precipitate from solution. Collect and combine all solid material to give 1.31 g, 71% yield of 4-cyano-benzoic acid iV-[2-(3-iodo-phenyl)-acetyl]-hydrazide as a powder.

According to the analysis of related databases, 1878-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KIRRANE, JR., Thomas Martin; MARSHALL, Daniel Richard; SIBLEY, Robert; SNOW, Roger John; SOLEYMANZADEH, Fariba; SORCEK, Ronald John; WO2012/54367; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com