Month: October 2020

5471-81-8, 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 5471-81-8 as follows.

General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3.

According to the analysis of related databases, Methyl 4-iodo-3-methylbenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Ze-Shui; Qian, Guangyin; Gao, Qianwen; Wang, Peng; Cheng, Hong-Gang; Hua, Yu; Zhou, Qianghui; Tetrahedron; vol. 75; 12; (2019); p. 1774 – 1780;,
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 77317-55-6 as follows. 77317-55-6

Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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 31599-60-7, 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.To a suspension of 8-iodo-l ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11) (0.645 g, 2.13 mmol) in methanol ( 1 8 mL) slowly SOCI2 ( 1.07 ml, 14.92 mmol) was added within 10 min. The reaction mixture was stirred at room temperature for 16 h, evaporated, and the residue was dissolved in a mixture of IN NaHC03 solution (30 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 ^ 15 mL). The organic extracts were combined, washed successively with water (20 mL), brine (20 mL), and dried (Na2S04). The solvents were evaporated to give compound 12 (0.570 g, 84%) which was used in the next step without further purification. NMR (CDCI3) delta: 7.67 (d, J=7.8 Hz, IH), 7.10 (d, J=7.5 Hz, I H), 6.87 (t, J=7.7 Hz, IH), 4.07 (d, 16.6 Hz, IH), 3.87 (d, J=16.6 Hz, I H), 3.78 (s, 3H), 3.71 (dd, J=9.4, 5.0 Hz, I H), 3.04 (dd, J=16.5, 5.0 Hz, IH), 2.97 (dd, J=l 6.5, 9.4 Hz, IH). LCMS (ESI) m/z: 318 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative methyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate). LCMS (ESI) m/z: 270 [M+H]+.A mixture of methyl 8-iodo-1, 2,3,4- tetrahydroisoquinoline-3-carboxylate (12) (0.570 g, 1 .8 mmol) and 2,3-dichloro-5,6-dicyano- 1 ,4-benzoquinone (DDQ) (0.449 g, 2.0 mmol) in toluene (20 mL) was refluxed for 6 h. To the reaction mixture was added another portion of DDQ (0.100 g, 0.45 mmol) and the refluxing was continued for 16 h. The mixture was allowed to cool to room temperature; the precipitate was filtered and washed with a small amount of toluene. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 100:0 to 100: …

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-Iodo-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); 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

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

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

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

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

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

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