Tag: M.W=200-300

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

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

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

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

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