Author: Jessica.F

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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 624-75-9

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (300 mg, 0.89 mmol), phenylboronic acid (0.12 g, 0.974 mmol), dichlorobis(triphenylphosphine)palladium (II) (31 mg, 0.044 mmol) and potassium carbonate (130 mg, 0.89 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:3, v/v): (166 mg, 74%); m.p. 55-56 C; 1H NMR (CDCl3) delta 2.32 (s, 3H), 3.71 (s, 3H), 5.14 (s, 2H), 6.79 (s, 1H), 6.84 (s, 1H), 6.96 (s, 1H), 7.13 (d, J=4.9 Hz, 1H), 7.41-7.48 (m, 3H), 7.65 (s, 1H), 7.79 (s, 1H), 7.88 (d, J=6.9 Hz, 2H), 8.61 (d, J=5.1 Hz, 1H); 13C NMR (CDCl3) delta21.51, 39.86, 55.25, 110.90, 113.61, 115.61, 119.78, 120.42, 121.24, 121.76, 126.89, 128.78, 129.11, 130.05, 132.90, 139.19, 139.98, 140.77, 149.89, 151.46, 157.75, 159.75.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 2043-57-4, These common heterocyclic compound, 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, 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.

The entire procedure including the isolation and characterization of the product was performed under an inert atmosphere (N2). n-BuLi (0.94 mL, 2.4 mmol, 1.0 equiv, 2.5 mol/L solution in hexane) was added at r.t. to a solution of Ph2PH (438 mg, 2.40 mmol, 1.0 equiv) in abs THF (2 mL). After stirring the mixture for 5 min at 23 C, perfluorinated iodide 19 (1.12 g, 2.40 mmol, 1.0 equiv) was added and the mixture was further stirred for 17 h at 23 C. The mixture was then filtered using a reversible frit and the resulting solution was evaporated to furnish the product 20 (1.11 g, 2.09 mmol, 89%) as an off-white solid; mp 40 C. IR (ATR): 3072 (w), 1482 (w), 1439 (w), 1364 (w), 1235 (m), 1182 (s), 1139 (s), 1121 (m), 1070 (m), 1028 (w), 925 (w), 847 (w), 746 (m), 735 (m), 723 (m), 693 cm-1 (s). 1H NMR (300 MHz, CDCl3): delta = 2.05-2.23 (m, 2 H), 2.24-2.37 (m, 2 H), 7.33-7.41 (m, 6 H), 7.42-7.51 (m, 4 H). 31P{1H} NMR (203 MHz, CDCl3): delta = -16.05 (s). The 13C NMR spectrum was in accordance with literature data. HRMS (ESI): m/z [M + Na]+ calcd for C20H14F13NaP: 555.0523; found: 555.0529.

The synthetic route of 2043-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alpers, Torben; Muesmann, Thomas W. T.; Temme, Oliver; Christoffers, Jens; Synthesis; vol. 50; 17; (2018); p. 3531 – 3539;,
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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-2-iodobenzoic acid

A solution of 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

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 21740-00-1.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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