Category: iodides-buliding-blocks

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. 3032-81-3 name is 1,3-Dichloro-5-iodobenzene, 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. 3032-81-3

Step A Synthesis of 5-hydroxy-5-(3,5-dichlorophenyl)hexanenitrile as an intermediate The Grignard reagent of 3,5-dichlorophenyl iodide was prepared by the reaction of 20.0 grams (0.073 mole) of 3,5-dichlorophenyl iodide and 1.8 grams (0.073 mole) of magnesium turnings in 350 mL of diethyl ether. The reaction mixture was heated at reflux for about three hours and then allowed to cool to ambient temperature. To the Grignard reagent, with stirring, was added dropwise during a 15 minute period a solution of 8.4 mL (0.073 mole) of 5-oxohexanenitrile in 25 mL of diethyl ether. The exothermic reaction caused the reaction mixture temperature to rise to about 30¡ã C. Upon completion of addition, the reaction mixture was stirred for one hour and then was poured into 400 mL of water. The mixture was made acidic with about 80 mL of aqueous 2N hydrochloric acid and extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chroma-tography on silica gel, using 5percent diethyl ether in methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 8.4 grams of 5-hydroxy-5-(3,5-dichlorophenyl)hexanenitrile. The NMR spectrum was consistent with the proposed structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3032-81-3, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; US5521192; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-75-9 name is 2-Iodoacetonitrile, 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. 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 (320 mg, 0.95 mmol), 2-acetylphenylboronic 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): (152 mg, 61%); m.p. 63-64 C.; 1H NMR (CDCl3) delta 2.19 (s, 3H), 2.28 (s, 3H), 3.70 (s, 3H), 5.16 (s, 2H), 6.75 (s, 1H), 6.79 (s, 1H), 6.90 (s, 1H), 7.11 (d, J=4.1 Hz, 1H), 7.40-7.55 (m, 4H), 7.65 (dd, J=4.8, 7.2 Hz, 1H), 7.81 (s, 1H), 8.48 (d, J=5.1 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodoacetonitrile, 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

Adding some certain compound to certain chemical reactions, such as: 73334-07-3, name is N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide, 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 73334-07-3. 73334-07-3

12,000 g of iopromide, pure mother liquor (solid content about 6.2%), is concentrated by evaporation in a vacuum to form viscous oil of 892 g. 877 g of this residue is mixed in a suitable reaction vessel at a bath temperature of 65 C. with 439 ml of 1-propanol while being stirred. After inoculation with 0.73 g of iopromide, it is fully stirred for another 48 hours at a bath temperature of 65 C. The crystal suspension is then cooled to 20 C., stirred for I hour at this temperature and suctioned off via a suction filter. After washing with 4 portions of 110 ml of ethanol, the secondary crystallizate is dried at 40 C. in a vacuum-drying oven. Yield: 363.8 g (about 52% of the experiment)

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 N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide.

Reference:
Patent; Kagerer, Hartmut; Dembeck, Meike; Seba, Harmut; Ortmann, Ingo; US2007/265470; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1878-69-9,Some common heterocyclic compound, 1878-69-9, name is 2-(3-Iodophenyl)acetic 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.

In a 100 mL hydrothermal synthesis reactor, sodium hydroxide (3 mmol) and water (5 mL) were added.After stirring and stirring, m-iodophenylacetic acid (0.5 mmol) and cuprous oxide (0.05 mmol) were added.White lignan (0.05 mmol), the reaction was stirred at 100 C for 6 hours.After cooling, the pH was adjusted to 2 with dilute hydrochloric acid and extracted with ethyl acetate.The extract is concentrated and subjected to column chromatography to obtain m-hydroxyphenylacetic acid.54.0 mg, yield 71%.

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

Reference:
Patent; Shenyang Pharmaceutical University; Yunnan Tropical Crop Science Institute; Chen Guoliang; Wu Ying; Bao Xuefei; Li Guohua; Liang Xinjie; Jiang Shikuan; Zhou Qifan; Du Fangyu; (11 pag.)CN109970542; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 6293-83-0, name is 2-Iodo-4-nitroaniline, I believe this compound will play a more active role in future production and life. 6293-83-0

Example 6 (examples of the reaction formula (3)) [of 18] To a 2-iodo-4-nitroaniline 12 (7. 50 g, 28. 4 mmol), bis(triphenylphosphine)palladium dichloride (99. 6mg,0 ? 142 mmol) and copper(I) iodide (54. 1 mg, 0. 284 mmol) in ethyl acetate (49. 9 mL) solution at room temperature, the diethylamine (10. 4 g, 142 mmol) and the terminal acetylene 11 (11. 5g, 42. 6 mmol) in toluene (28.9mL) was added. Furthermore, the reaction mixture was heated to 50 C, and stirred for 6 hours. To the resulting reaction mixed solution is added with activated carbon (0.750g), in 50 C is filtered to remove the activated carbon and the reaction residue, adding water in the filtrate (22.5 ml), separating the organic phase. Furthermore, the solvent of the organic phase the distill goes under reduced pressure, the crude product obtained by adding toluene (46.2 ml), activated carbon (1.15g), in not more than 80 C lower filtering to remove the temperature of the activated carbon, the target is obtained by re-crystallization from filtrate nitryl body 13 (10.3g, 25.2 mmol, yield 89%). Nitro compound 13 through the structure of1H-NMR analysis identified, with the above-mentioned embodiment of the results of 5 the nitro compound obtained in 13 the1H-NMR completely identical.

The chemical industry reduces the impact on the environment during synthesis 6293-83-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Takayama, Yuki; Nagao, Masato; (20 pag.)CN103068795; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

914225-70-0,Some common heterocyclic compound, 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, molecular formula is C8H6FIO, 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 1051-(2-Acetyl-4-fl ro-phenyl)-pyrrolidin-2-one1 ,4-Dioxane (50 ml_) was degassed by heating briefly to reflux and bubbling nitrogen gas through the solvent for 10 minutes, whilst it cooled to room temperature. Cul (180 mg, 5 mol%), glycine (284 mg, 20 mol%), 2-pyrrolidinone (1.73ml_, 22.73 mmol), K3PO4 (10.05 g, 47.35 mmol) and 1-(5-fluoro-2-iodo-phenyl)-ethanone (5.0 g, 18.94 mmol) were added sequentially to the solvent and the reaction mixture was heated at 100C under N2 for 10 hours. The reaction mixture was filtered through a celite plug, eluting with EtOAc and the filtrate was concentrated. The crude product was purified by flash chromatography (5% MeOH in DCM) to give the title compound (2.02 g, 48% yield) as a yellow oil1H NMR (400 MHz, CDCI3): delta ppm 2.20 (2H, pentet), 2.47 (2H, t), 2.54 (3H, s), 3.83 (2H, t), 7.17-7.21 (2H ,m), 7.28-7.32 (1 H, m). MS:: m/z 222 [MH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(5-Fluoro-2-iodophenyl)ethanone, its application will become more common.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
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 71838-16-9 as follows. 71838-16-9

General procedure: A mixture of carbazole(1.67 g, 10 mmol), 2-bromoiodobenzene (4.2 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), CuI (0.95 g, 5 mmol) and DMA (100 mL) in a 250 mL three-necked flask was heated at 130 C for 48 h under nitrogen. After cooling, it was poured into water (200 mL) and extracted with CH2Cl2, the combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was isolated by column chromatography (PE) to afford white powder.

According to the analysis of related databases, 71838-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5326-39-6, 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. 5326-39-6, name is 1-Iodo-4-methyl-2-nitrobenzene, A new synthetic method of this compound is introduced below.

General procedure: To a mixture of 3-bromo-2-nitrotoluene 15c (2.13g, 9.86mmol) and 1,4-dioxane (50mL) were added 2-imidazolidone 16a (4.01g, 46.6mmol), Cs2CO3 (4.71g, 14.5mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 400mg, 0.437mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (XantPhos; 503mg, 0.869mmol) under argon atmosphere. The mixture was stirred at 100C for 19.5h. After cooling to room temperature, the mixture was filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3), and concentrated in vacuo. To a mixture of the residue in EtOH (12mL) and H2O (3.0mL) were added FeCl3¡¤6H2O (99.0mg, 0.366mmol), N2H4¡¤H2O (1.10mL, 22.7mmol), and activated carbon (102mg). The mixture was stirred under reflux for 14h. After cooling to room temperature, the mixture was filtered through a pad of Celite. The filtrate was diluted with EtOAc, and washed with H2O and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. A mixture of the residue and POCl3 (2.00mL, 21.8mmol) was stirred at 100C for 5h. After cooling to room temperature, the reaction mixture was concentrated in vacuo. 1M NaOH aqueous solution was added to the residue followed by extraction with CHCl3/MeOH co-solvent. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-3% MeOH in CHCl3) to give 17c (345mg, 20% in 3 steps) as a 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:
Article; Chino, Ayaka; Honda, Shugo; Morita, Masataka; Yonezawa, Koichi; Hamaguchi, Wataru; Amano, Yasushi; Moriguchi, Hiroyuki; Yamazaki, Mayako; Aota, Masaki; Tomishima, Masaki; Masuda, Naoyuki; Bioorganic and Medicinal Chemistry; vol. 27; 16; (2019); p. 3692 – 3706;,
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. 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, A new synthetic method of this compound is introduced below., 25252-00-0

Example I 4-Bromo-3-hydroxvmethyl- 1 iodo-benzeneOxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo5-iodo-benzoic acid (49.5 g) in CH2CI2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h Then the solution is concentrated under reduced pressure and the residue is dissolved in THE (100 mL). The resulting solution is cooled in an ice-bath andLiBH4 (3A g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product.Yield: 47.0 g (99% of theory)

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; BOEHRINGER INGELHEIM VETMEDICA GMBH; ECKHARDT, Matthias; BUTZ, Tanja; HIMMELSBACH, Frank; MARTIN, Hans-Juergen; WO2014/16381; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

629-09-4, The chemical industry reduces the impact on the environment during synthesis 629-09-4, name is 1,6-Diiodohexane, I believe this compound will play a more active role in future production and life.

1,2-Dihydro-4-(6-iodohexyloxy)-1,2-dioxonaphthalene (5) A mixture of 1,6-diiodohexane (10.14 g, 30 mmol) and the silver salt of 2-hydroxy-1,4-naphthoquinone (2.81 g, 10 mmol) in benzene (60 mL) was stirred for 12 h at room temperature. The reacton mixture was filtered through Celite, concentrated in vacuo, and purified by flash chromatography (hexane/EtOAc 4:1) to give a yellow solid (2,19 g, 57%); mp 85-87 C.; 1H NMR (CDCl3) 8.12 (dd, J=6.5, 1.0 Hz, 1H), 7.86 (dd, J=6.9, 0.9 Hz, 1H), 7.70 (dt, J=7.6, 1.5 Hz, 1H), 7.58 (dt, J=7.5, 1.3 Hz, 1H), 5.95 (s, 1H), 4.15 (t, J=6.3, 2H), 3.22 (t, J=6.9 Hz, 2H), 1.80-2.05 (m, 4H), 1.45-2.10 (m, 4H).

The chemical industry reduces the impact on the environment during synthesis 1,6-Diiodohexane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SLIL Biomedical Corporation; US6482943; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com