Category: iodides-buliding-blocks

628-21-7, These common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, 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.

In three 250ml flask anthrone 19.4g (0.1mol), 150ml dried THF, was added with stirring diiodobutane (34.1g, 0.11mol), potassium tert-butoxide and 26.8g (0.24mol), the reaction was stirred for 3 hours at room temperature, the reaction was refluxed for 3 hours. Saturated ammonium chloride solution was added to quench the reaction, extracted with ethyl acetate, dried liquid separation, column chromatography to obtain 13.6 g of a white solid, a yield of 55%.

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 628-21-7.

Reference:
Patent; KUNSHAN VISIONOX DISPLAY CO., LTD.; BEIJING VISIONOX TECHNOLOGY CO., LTD; Tsinghua University; Qiu, Yong; Fan, Hongtao; Duan, Lian; (49 pag.)CN103172524; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 1878-94-0, name is 2-(4-Iodophenoxy)acetic acid, molecular formula is C8H7IO3, 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. 1878-94-0.

The reaction mixture of N-deacetylthiocolchicine (24 mg, 0.064 mmol), 4-iodophenoxyacetic acid (41 mg, 0.15 mmol), EDCI (29 mg), DMAP (2 mg, 0.2 mmol) and dichloromethane (3 ml) was stirred at room temperature for 20 h. Then dichloromethane (20 ml) was added. Organic layer was washed with H2O, 5% Na2CO3 and brine, and then dried over MgSO4. After the solvent was removed under vacuum, the residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether) to afford 35 mg N-Deacetyl-N-(4-iodophenoxyacetyl)thiocolchicine. [0571] The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz).

The synthetic route of 2-(4-Iodophenoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yang, Li-Xi; US2004/204370; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2265-93-2, 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. 2265-93-2, name is 2,4-Difluoroiodobenzene, A new synthetic method of this compound is introduced below.

To toluene 3.0mL solution of tert-butyl 2-amino-4-phenethyl benzoate 0.10g were added 2,4-difluoro-1-iodobenzene 0.10mL, cesium carbonate 0.22g, tris(dibenzylideneacetone)dipalladium(0) 3mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl 8mg, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 3mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8mg were added to it, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate:acetic acid=20:1:1] to give tert-butyl 2-(2,4-difluoroanilino)-4-phenethylbenzoate. Trifluoroacetic acid 10mL was added to the obtained tert-butyl 2-(2,4-difluoroanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, methanol was added to the obtained residue, and solid matter was filtrated to give 2-(2,4-difluoroanilino)-4-phenethylbenzoic acid 59mg of white solid. 1H-NMR(DMSO-d6) delta value: 2.82(4H,s),6.65(1H,s),6.70(1H,dd,J=8.1,1.5Hz),7.05(1H,t dd,J=8.6,2.8,1.3Hz),7.14-7.21(3H,m),7.23-7.30(3H,m),7.37(1H,ddd,J=11.1,8.9,2.8Hz),7.81(1H,d,J=8. 1Hz),9.46(1H,s),12.85-13.20(1H,broad).

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; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 74-88-4, name is Iodomethane, molecular formula is CH3I, 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. 74-88-4

EXAMPLE 29 Preparation of 6-methyl-1-[(3-iodo-4,5-dimethoxy-phenyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole STR79 To a stirred, cooled (0 C.) solution of iodovanillin (10.0 g, 35.96 mmol.) in dimethylformamide (50 mL) was added anhydrous potassium carbonate (20.0 g, 143.86 mmol.) followed by iodomethane (3.11 mL, 50.0 mmol.). The mixture was allowed to warm to ambient temperature and stir for 14H. The mixture was poured into diethyl ether (500 mL) and washed with water (3*150 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure to afford 3-iodo-4,5-dimethoxybenzaldehyde (9.5 g) as a yellow oil which solidified upon standing and was used without further purification. STR80

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74-88-4, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5500431; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 34683-73-3, name is 1-Chloro-6-iodohexane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 34683-73-3

6-(3’4′-dibenzyloxyflavon-3-yl)-hexyltrimethylammoniumchloride (6g) 4b was alkylated using 1-chloro-6-iodohexane, employing the same method as described for 5d. The crude product was purified by column chromatography (CH2Cl2) to give 1.6 g (94%) 3-(6-chlorohexyloxy)-3′,4′-dibenzyloxyflavone. 1H NMR (CDCl3): delta 1.36 (m, 4H, CH2), 1.68 (m, 4H, CH2), 3.47 (t, 2H, J=6 Hz, CH2Cl), 3.99 (t, 2H, J=6 Hz, OCH2), 5.23 (s, 2H, OCH2Ph), 5.27 (s, 2H, OCH2Ph), 7.03 (d, 1H, J=8 Hz, C5’H), 7.25-7.5 (m, 12H, 2* OCH2Ph+C6H, C8H), 7.66 (dt, 1H, J=7 Hz, 2 Hz, C7H), 7.71 (dd, 1H, J=8 Hz, 1 Hz, C6’H), 7.80 (d, 1H, J=1 Hz, C2’H), 8.23 (dd, 1H, J=7 Hz, 2 Hz, CSH).

The synthetic route of 34683-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vereniging christelijk wetenschappelijk anderwijs; US2002/147353; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

351003-36-6, 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. 351003-36-6 name is 2-Fluoro-5-iodobenzonitrile, 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.

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

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

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
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. 619-58-9, name is 4-Iodobenzoic acid, A new synthetic method of this compound is introduced below., 619-58-9

General procedure: A solution of 4-iodotoluene (1.05 g, 4.83 mmol) in a mix of 19.3 mL of n-Bu4NOH 1.5 M aqueous solution and 19.3 mL of DMSO (for an overall 0.125 M solution vs 4-iodotoluene) was prepared. Using Flow commander software, a continuous flow experiment was designed in order to control the flow stream of the pump matching 20 min of residence time (the flow stream was set at 0.50 mL/min). 37 mL of the reaction solution was injected (corresponding to 4.63 mmol of 4-iodotoluene that will be used to calculate the isolated yield; this method being used in order to maximise the reproducibility for the reported yield)using direct injection mode and the reagent stream was pumped into the 10 mL copper reactor (1.0 mm i.d.) at 150 C. 2 X 8 bar back pressure regulators (BPR) were placed in series atthe end of the reactor, allowing safe heating of the solvent. 48 mL of the crude reaction solution was then collected into 100 mL glass vial. A reconditioning, consisting of 3 mL of DMF followed by 3 mL of a 10% aqueous acetic acid solution, was run after the experiment in order to clean the reactor. The crude reaction solution was then acidified to pH = 1 with 2 N HCl. Water (150 mL) was added and the mixture was extracted with Et2O (3 X 150 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under vacuum. The crude mixture was purified by automated flash column chromatography using a 24 g column and a 30-80% DCM/Hexanes gradient affording 406 mg of 2a (81% yield).

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; Cyr, Patrick; Charette, Andre B.; Synlett; vol. 25; 10; (2014); p. 1409 – 1412;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

25252-00-0, Adding some certain compound to certain chemical reactions, such as: 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, 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 25252-00-0.

To the solution of 2-bromo-5-iodo-benzoic acid (10 g, 31 mmol) in methanol (100 ml) was added thionyl chloride (5 ml, 68 mmol). The mixture was heated at 55C for 12 hours. The solvent and reagent were removed under reduced pressure and the mixture was diluted with EtOAc. The organic solution was washed with saturated sodium bicarbonate, water, and brine, and was dried with sodium sulfate. Concentration gave 2- bromo-5-iodo-benzoic acid methyl ester (10.5 g).

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 25252-00-0.

Reference:
Patent; GILEAD SCIENCES, INC.; GUO, Hongyan; KATO, Darryl; KIRSCHBERG, Thorsten, A.; LIU, Hongtao; LINK, John, O.; MITCHELL, Michael, L.; PARRISH, Jay, P.; SQUIRES, Neil; SUN, Jianyu; TAYLOR, James; BACON, Elizabeth, M.; CANALES, Eda; CHO, Aesop; KIM, Choung, U.; COTTELL, Jeromy, J.; DESAI, Manoj, C.; HALCOMB, Randall, L.; KRYGOWSKI, Evan, S.; LAZERWITH, Scott, E.; LIU, Qi; MACKMAN, Richard; PYUN, Hyung-Jung; SAUGIER, Joseph, H.; TRENKLE, James, D.; TSE, Winston, C.; VIVIAN, Randall, W.; SCHROEDER, Scott, D.; WATKINS, William, J.; XU, Lianhong; YANG, Zheng-Yu; KELLAR, Terry; SHENG, Xiaoning; CLARKE, Michael, O’Neil, Hanrahan; CHOU, Chien-hung; GRAUPE, Michael; JIN, Haolun; MCFADDEN, Ryan; MISH, Michael, R.; METOBO, Samuel, E.; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WO2010/132601; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

To a stirred solution of methyl 6-iodoanthranilate (53) (4.46 g, 16.1 mmol) in ethyl orthoformate (8.92 mL, 53.5 mmol) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (1.16 g, 8.05 mmol). The mixture was stirred at 80 C for 45 min. After cooling to room temperature, the yellow precipitate was filtered and washed with ethanol (2 x 10 mL) to give methyl 2-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)amino]-5-iodobenzoate (54) (3.31 g, 7.68 mmol) as a yellow solid. Yield 95%; mp 206-208 C; IR (KBr) nu 1198, 1227, 1251, 1284, 1429, 1585, 1607, 1685, 3100-3250 cm-1; 1HNMR (200 MHz, CDCl3) delta 1.07 (s, 6H, (CH3)2C), 3.98 (s, 3H, CH3O), 7.23 (d, 1H, J = 8.8 Hz), 7.86 (dd, 1H, J = 2.0, 8.8 Hz, H-3), 8.38 (d, 1H, J = 2.0 Hz, H-4), 8.65 (d, 1H, J = 14.0 Hz, C=CH-NH), 13.1 (d, 1H, J = 14.0 Hz, NH); 13C NMR (50 MHz, CDCl3) delta 27.2 ((CH3)2C), 53.2 (CH3O), 88.5 (C-5), 89.9 (C=CH-NH), 105.1 ((CH3)2C), 117.6 (C-3), 119.7 (C-1), 139.5 (C-2), 140.8 (C-6), 143.2 (C-4), 150.4 (C=CH-NH) 163.6 (CO), 164.0 (CO), 165.3 (CO); ESI-MS m/z 373.89 [M-CH3O-CO + H]+.

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3058-39-7, 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. 3058-39-7, name is 4-Iodobenzonitrile, A new synthetic method of this compound is introduced below.

Example 3; Preparation of Organic Compound by Using Silicon-Based Cross-Coupling Reagents 1a to 1i of the Present Invention; The silicon-based cross-coupling reagents 1a to 1i of the present invention were used to carry out cross coupling reaction with an organic halide I-R10, thereby preparing various kinds of organic compounds. Table 1 shows reaction times, yields, a silicon-based cross-coupling reagent R1 used and an organic halide R10. Note that, in Table 1, product numbers correspond to the numbers of the following substances respectively.; Any one of the silicon-based cross-coupling reagents 1a to 1i (1.1 mmol) and the organic halide (1.0 mmol) were sequentially added to a mixture of K2CO3 (304 mg, 2.2 mmol), tri-2-furilic phosphine (4.6 mg, 20 mumol), and PdCl2 (1.8 mg, 10 mumol) in DMSO (2.5 mL), and the resulting mixture was stirred at 35¡ã C. When each of the times shown in Table 1 had passed, the resulting mixture was diluted with diethyl ether and was washed with water and brine, and then was dried over anhydrous MgSO4. After concentration under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining organic compounds p1 to p24 which were cross-coupling products respectively corresponding to yields shown in Table 1. The following shows chemical formulas and characteristic data of the resultant organic compounds p1 to p22 and p24.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nakao, Yoshiaki; Hiyama, Tamejiro; US2009/69577; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com