Category: iodides-buliding-blocks

The chemical industry reduces the impact on the environment during synthesis 624-75-9, name is 2-Iodoacetonitrile, I believe this compound will play a more active role in future production and life. 624-75-9

e) To a solution of 7-benzyloxymethyl-8-(4-hydroxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione (1 g, 2.2 mmol) in tetrahydrofuran (20 ml) was added potassium t-butoxide (0.28 g, 2.4 mmol), and the mixture stirred for 30 minutes at room temperature. Iodoacetonitrile (0.38 g, 2.23 mmol) was then added, and the mixture stirred for 16 hours at room temperature. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and passed through a silica gel plug, to provide 7-benzyloxymethyl-8-(4-cyanomethoxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione, a compound of formula (7)

The chemical industry reduces the impact on the environment during synthesis 624-75-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kalla, Rao; Perry, Thao; Elzein, Elfatih; Varkhedkar, Vaibhav; Li, Xiaofen; Ibrahim, Prabha; Palle, Venkata; Xiao, Dengming; Zablocki, Jeff; US2005/261316; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, 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 624-75-9 as follows.

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 (320 mg, 0.95 mmol), 4-acetylphenyl boronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 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¡Á3). 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, 1:2, v/v): (93 mg, 75%); m.p. 156-157 C.; 1H NMR (CDCl3) delta 2.42 (s, 3H), 2.65 (s, 3H), 3.82 (s, 3H), 4.97 (s, 2H), 6.75 (s, 1H), 6.82 (s, 1H), 6.96 (s, 1H), 7.12 (d, J=4.9 Hz, 1H), 7.60 (s, 1H), 7.87 (d, J=8.1 Hz, 2H), 7.99-8.02 (m, 3H), 8.56 (d, J=5.1 Hz, 1H); 13C NMR (CDCl3) delta 21.60, 26.78, 37.78, 55.52, 112.34, 114.02, 116.86, 118.62, 119.33, 120.38, 122.67, 126.90, 128.76, 129.01, 137.12, 139.56, 140.61, 141.58, 141.96, 143.49, 150.20, 156.29, 160.54, 197.88.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 624-75-9, and friends who are interested can also refer to it.

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

1643-29-4, A common heterocyclic compound, 1643-29-4, name is 3-(4-Iodophenyl)propanoic acid, 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.

Next, the 4-iodohydrocinnamic acid is methylated. 350 g of the produced 4-iodohydrocinnamic acid is wet with 250 g water. To the mixture is added 1.4 L methanol and 1.5 g p-toluene sulfonic acid in water. The mixture is refluxed overnight, and excess methanol is removed. 500 mL toluene is added and mixed, and then excess toluene and water is removed. Next, 500 mL methanol is added to the mixture. The mixture is refluxed for 30 minutes, after which excess methanol is again removed. The result is 162 g of methyl-4-iodohydrocinnamic acid (61% purity).

The synthetic route of 1643-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XEROX CORPORATION; US2006/111582; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

672-57-1, 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 672-57-1 as follows.

Three point eight (3.8) ml of n-butyllithium (2.6 M hexane solution) was added dropwise to a mixture of 3.00 gof 1-chloro-2-iodo-4-(trifluoromethyl)benzene and 15 ml of tetrahydrofuran at -70C, followed by stirring for 30 minutes.Thereafter, a mixture of 1.69 g of N-methoxy-N-methyltrifluoroacetamide and 5 ml of tetrahydrofuran was added dropwisethereto at -70C. Subsequently, after the reaction mixture was stirred for 1 hour at room temperature, water was addedthereto, and extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, driedover magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gelcolumn chromatography, thereby obtaining 1.66 g of 2,2,2-trifluoro-1-[2-chloro-5-(trifluoromethyl)phenyl]ethanone.

According to the analysis of related databases, 1-Chloro-2-iodo-4-(trifluoromethyl)benzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

627-32-7,Some common heterocyclic compound, 627-32-7, name is 3-Iodo-1-propanol, molecular formula is C3H7IO, 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.

Cesium carbonate [(5.] 54 g) is added to a solution [OFN (4-CHLOROBENZYL)-4-HYDROXY 2-] (hydroxymethyl) thieno [2, [3-B]] [PYRIDINE-5-CARBOXAMIDE] (5.23 g, prepared as described in US 6,239, 142) and 2-(3-iodopropoxy)tetrahydro-2H-pyran (4.32 g, prepared by mixing equal molar amounts of 2-iodopropanol and 3, 4-dihydro-2H-pyran) in DMF (20 mL). The mixture is heated at [60 C] for 4 hours. The solvent is evaporated and the residue is dissolved in 10% [MEOH] in [CH2C12.] The mixture is washed with water and the organic layer is dried (MgSO4), filtered, and concentrated. The crude product is purified by column chromatography [(CH2CLJMETHANOL,] [95/5)] followed by recrystallization from EtOAc to afford 4.82 g of the title compound as white crystals. Physical characteristics. 1H NMR (400 [MHZ,] DMSO-d6) 8 10.55, 8.71, 7.39, 7.33, 7.29, 5.79, 4. [70,] 4.53, 4.49, 4. [38, 3.] 68,3. [37,] 2.11, 1.63, 1.53, 1.40 ; MS [(EI)] m/z 490 [(MF)] ; Anal. Found: C, 58.74 ; H, 5.66 ; N, 5.61.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-1-propanol, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; FLECK, Bruce, Francis; WO2004/22567; (2004); 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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., 624-75-9

Step 2: Synthesis of 2-(2-chloro-6-morpholino-9H-purin-9-yl)acetonitrile (14c)To a solution of 13a (1.18 g, 4.94 mmol) in acetonitrile/DMSO (19:1) was added 2- iodoacetonitrile (0.71 mL, 9.87 mmol) and K2C03 (1.36 g, 9.87 mmol). The resulting mixture was heated at 60CC for 3 h. Then the solvents were removed in vacuo and water was added. The aqueous layer was extracted with DCM (x2) and the combined organic layers was washed with brine (xl), dried over MgSO4 and evaporated in vacuo. The crude oil was purified by flash chromatography(silica, 50% ethyl acetate in hexanes) to afford 14c (1.31 g, 95%) as pale brown solid.

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; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; WANG, Haishan; CHEN, Dizhong; SOH, Chang Kai; WO2015/137887; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 62720-29-0, name is 1,3-Dibromo-5-fluoro-2-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. 62720-29-0

A solution of l,3-dibromo-5-fluoro-2-iodobenzene (50 g, 132 mmol ) in anhydrous toluene (300 mL) cooled to -35 C was added the solution of isopropylmagnesium chloride (84 mL, 171 mmol, 2.0 M in diethyl ether ) over a period of 30 minutes while maintaining the internal temperature below -25C. A clear brown solution was obtained. Stirring was continued for 1.5 h. Then anhydrous DMF (34 mL, 436 mmol ) was added over a period of 30 minutes. The temperature of the reaction mixture increased to -19C. The reaction mixture was warmed to 10C (room temper-ature) over lh and stirred at this temperature for 1.5 h. The reaction was quenched with saturated aqueous NH4C1 (100 mL), filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate: from 50: 1 to 20: 1) to give 197a ( 20 g, yield 54%) as a yellow solid.

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 62720-29-0.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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. 612-55-5.

General procedure: A 10mL-sealed tube was charged with aryl iodides or bromides (1mmol), CuI (19mg, 0.1mmol) in NH4OH (1.5mL, 27% NH3 in H2O) and PEG300 (0.5g). The tube was flushed with Ar gas before being capped. The solution was stirred for the given times at 130C or 110C. The resulting suspension was cooled to room temperature and saturated aqueous Na2SO4 solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL¡Á3). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (hexanes/EtOAc=5/1?1/2 or EtOAc) to give the desired primary arylamines.

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

Reference:
Article; Jung, Hee Seon; Yun, Taeil; Cho, Yungyeong; Jeon, Heung Bae; Tetrahedron; vol. 72; 40; (2016); p. 5988 – 5993;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, A common compound: 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Indole (1.0 mmol),Cs2CO3 (1.0 mmol), 2-bromopyridine (1.5 mmol), Cu2O (0.1 mmol), and DMA (3 mL) were added to a 5-mL vial. The vial was sealed with a crimp cap and placed in a Biotage initiator microwave cavity. After irradiation at 200C for the appropriate time and subsequent cooling, the reaction mixture was diluted with saturated aqueous ammonium chloride. Products were isolated by extraction into ethylacetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. Products were purified by silica gel column chromatography using a hexane:ethyl acetate solvent. N-2-pyridylindole (2a) was obtained (80% yield) as yellow oil;

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, 1,2-Difluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kwon, Jae-Kwan; Lee, Jin -Hee; Kim, Tae Sung; Yum, Eul Kgun; Park, Hee Jung; Bulletin of the Korean Chemical Society; vol. 37; 12; (2016); p. 1927 – 1933;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, The chemical industry reduces the impact on the environment during synthesis 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried screw cap test tube was charged with a magnetic stir bar, Pd(PPh3)2Cl2 (2 mol%), CuI (4 mol%), and K2CO3 (0.4mmol). The tube was then evacuated and backfilled with argon.The evacuated/backfill sequence was repeated two additional times. Under a counter-flow of argon, DMF (1 mL), iodoarene(1a, 0.2 mmol), and methyl propiolate (2a, 0.3 mmol) were added. The tube was placed in a preheated oil bath at 80 C, andthe mixture was stirred vigorously for 10 min. Then the screwcap was opened and 2-pyridyl ethyl ester (3a, 0.2 mmol) wasadded in air at 80 C. The mixture was allowed to react for another 8 h at 80 C in air atmosphere. After the reaction was finished, water (5 mL) was added, and the solution wasextracted with ethyl acetate (3 ¡Á 5 mL), the combined extractwas dried with anhydrous MgSO4. Solvent was removed, andthe residue was separated by column chromatography (petroleumether/ethyl acetate, 2:1) to give 4a (50 mg, 86%) as ayellow solid.

The chemical industry reduces the impact on the environment during synthesis 1,2-Difluoro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Zhengwang; Liu, Tanggao; Ma, Xiaoyue; Liang, Pei; Long, Lipeng; Ye, Min; Synlett; vol. 30; 7; (2019); p. 863 – 867;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com