Month: November 2020

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. 696-41-3 name is 3-Iodobenzaldehyde, 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. 696-41-3

To a suspension of NaH (60% dispersion in mineral oil) (120 mg, 3.0 mmol) in THF (20 mL) was added triethyl phosphonoacetate (436 muL, 2.2 mmol) dropwise. 3-iodo-benzaldehyde (465 mg, 2.0 mmol) was added after the bubbling has stopped. The reaction mixture was stirred at room temperature for 15 minutes. Solid NH 4Cl was added, followed by 1N HCl to quench the reaction. The mixture was taken up in ethyl acetate and water. The organic phase was washed with aqueous NaHCO 3, brine, dried (MgSO 4), filtered and concentrated under reduced pressure and purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1) to provide the titled compound (605 mg).

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

Reference:
Patent; Xin, Zhili; Liu, Gang; Pei, Zhonghua; Szczepankiewicz, Bruce G.; Serby, Michael D.; Zhao, Hongyu; US2004/214870; (2004); A1;,
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 82998-57-0 as follows. 82998-57-0

Add 1 equivalent of potassium t-butoxide to a 25 mL Schlenk reaction tube, add 2 mL of toluene under an argon atmosphere, stir for 30 min, remove the solvent, add 0.02 equivalent of anhydrous copper sulfate and 4.0 equivalent of potassium t-butoxide, and dry in vacuum for 15 minutes. 3 mL of benzonitrile and 1 mL of t-butanol were sequentially added under an argon atmosphere, 2 mmol of 3-iodo-4-methylbenzoic acid was in the reaction tube after adding polytetrafluoroethylene stopper was placed into an oil bath of the reaction 90 C for 24 h. After the reaction is completed, 4 equivalents of formic acid are added, and the solvent is removed by filtration and the residue is purified by column chromatography eluting with petroleum ether / methylene chloride / ethyl acetate (v: v: v = 5:10:1), 6-carboxy-2-phenyl-1H-indole was obtained as a white solid. The yield was 92%.

According to the analysis of related databases, 82998-57-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Kang Yanbiao; Shan Xianghuan; (12 pag.)CN108863894; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 64248-58-4

General procedure: A Schlenk flask equipped with asepta and a magnetic stir bar wasfilled with aryl halide (3.0 mmol), alkene (3.2 mmol), K2CO3(3.5 mmol) and PdLn-beta-CD 3 mol% catalyst in water (5 mL pure orplain). The reaction was refluxed for the appropriate time underaerobic conditions. After completion of the reaction was confirmedby TLC, the reaction mixturewas cooled to room temperature.The solvent was removed by rotary evaporator and extraction of theproduct was carried out using ethyl acetate. The ethyl acetate fractionwas separated and dried over anhydrous sodium sulphate. Theresulting crude product was purified using flash column chromatographyof silica gel 60-120mesh with n-hexane/ethyl acetate (8:2ratio) as the eluent and afforded the pure desired product. After extractionof product, catalyst was simply reprecipitated from theaqueous layer by the addition of 10 mL of acetone. The recoveredcatalyst was filtered, washed with acetone (3 ¡Á 5 mL) and dried ina vacuum at 70 C for 5 h and reused.

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:
Article; Dindulkar, Someshwar D.; Jeong, Daham; Kim, Hwanhee; Jung, Seunho; Carbohydrate Research; vol. 430; (2016); p. 85 – 94;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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 148870-57-9, 148870-57-9

7,8-Dimethoxy-3-[3-iodopropyl]-l,3-dihydro-2H-3-benzazepin-2-one (38g) and potassium carbonate (6Og) were added to a mixture of (S)-N-[(4,5-dimethoxybenzocyclobut-l-yl)-methyl]- 7V-(methyl)amine (2Og) and demineralized water (100ml) at room temperature. The reaction mixture was heated and stirred at 50-55 C for 12-16 hours. After completion of reaction, reaction mass was cooled to 25-30 0C and the product is extracted in ethyl acetate (100ml). The aqueous layer was further extracted with ethyl acetate (60ml). Combined ethyl acetate layers was acidified with aqueous hydrochloric acid and stirred. The layers were separated and pH of the aqueous layer was adjusted to 10.5-12.5 with aqueous sodium hydroxide solution. The aqueous layer is extracted with ethyl acetate (140ml + 60ml). Ethyl acetate was distilled out completely under vacuum to get the title compound.

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, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; WO2008/146308; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6293-83-0, 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. 6293-83-0 name is 2-Iodo-4-nitroaniline, 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: A mixture of 2-iodoaniline 1 (0.5 mmol) and Pd(OAc)2 (5.6 mg, 0.025 mmol, 5.0 mol%) in CH3CN (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature. Followed by the addition of ethyl acrylate 2a (100 mg, 1.0 mmol, 2.0 equiv) and triethylamine (101 mg, 1.0 mmol, 2.0 equiv), the mixture was stirred at 100 C until the reaction was finished. Then the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1 to 2:1) afforded the corresponding alkenylanilines 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4-nitroaniline, and friends who are interested can also refer to it.

Reference:
Article; Chen, Xia; Zhou, Xiao-Yu; Wang, Liang-Guang; Synthetic Communications; vol. 47; 22; (2017); p. 2096 – 2102;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

135050-44-1, 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 135050-44-1 as follows.

Step 1) N- (3-chloro-4-iodophenyl) methanesulfonamide To a solution of 3-chloro-4-iodoaniline (2.53 g, 10 mmol) in dichloromethane (20 mL) was added pyridine (0.87 g, 11 mmol) , followed by methylsulfonyl chloride (1.26 g, 11 mmol) at 0 . After the addition, the mixture was stirred at 0 for 2 hours. The reaction was quenched with water (20 mL) . The resulting mixture was extracted with DCM (150 mL) . The organic layer was washed with saturated aqueous NaCl (50 mL) and dried over anhydrous Na2SO4and concentrated in vacuo to give N- (3-chloro-4-iodophenyl) methanesulfonamide as a gray solid (3.0 g, 91) . MS (ESI, pos. ion) m/z: 331.8 [M+H]+.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; XIE, Hongming; WU, Xiwei; REN, Qingyun; ZHANG, Jiancun; (236 pag.)WO2015/197028; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 461-17-6, name is 1,1,1-Trifluoro-4-iodobutane, 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. 461-17-6

The alcohol of Example A13 (0.70 g, 1.85 mmol), tetrabutylammonium bromide (119 mg, 0.376 mmol), and KOH (311 mg, 5.55 mmol) were slurried in xylene (7.5 mL). Afterward, 4,4,4-trifluoro-1-iodobutane (1.32 g, 5.55 mmol) was added, and the reaction mixture was stirred in a sealed vial at 80 C. over the weekend. Subsequently, the mixture was filtered through celite and concentrated under N2. Chromatography (on silica, ethyl acetate/hexanes) afforded the ether in the form of a pale yellow oil (551.8 mg, 61.1% yield). NMR(CDCl3) delta 1.19-1.32 (m, 2H), 1.47-1.60 (m, 12H), 1.68 (d, 2H), 1.74-1.84 (m, 2H), 2.05-2.23 (m, 4H), 2.32 (d, 2H), 2.93 (dt, 2H), 3.39 (dt, 2H), 3.43 (dt, 4H), 3.76 (d, 2H), 3.96 (dd, 2H). ESMS m/z=488.42 (M+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, 461-17-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene, A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-l-iodo-2 -methyl -benzene (3.73 g, 12.6 mmol) in anhydrous tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M, 5.02 mL) at -70 C for 30 min. Then, (¡À)-2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (2.00 g, 11.4 mmol) in anhydrous tetrahydrofuran (10 mL) was added at -70 C. The reaction mixture was stirred at rt for 30 min. On completion, the mixture was quenched with water (20 mL) and concentrated in vacuo to remove the organic solvent. The aqueous phase was extracted with dichlorom ethane (3 X 100 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (dichloromethane:methanol = 100: 1) to give the title compound. NMR (400MHz, CDC13) delta = 7.42 – 7.30 (m, 2H), 7.04 (d, J= 8.0 Hz, 1H), 5.33 (d, J = 7.0 Hz, 1H), 5.15 (d, J= 6.8 Hz, 1H), 5.02 (d, J = 6.8 Hz, 1H), 4.90 (d, J = 7.0 Hz, 1H), 4.24 (s, 1H), 2.13 (s, 3H), 1.19 (s, 9H).

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; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (2017); A1;,
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 63262-06-6 as follows. 63262-06-6

To a solution of 1,4-dibromo-2,5-diiodo-benzene (15.0 g, 31 mmol) and ethynyl-trimethyl-silane (6.0 g, 62 mmol) in tetrahydrofuran (150 cm3) under nitrogen atmosphere at room temperature is added diisopropylamine (90 cm3, 640 mmol), copper(I)iodide (353 mg, 1.9 mmol) and bis(triphenylphosphine) palladium(II)chloride (60 mg, 0.9 mmol). The resulting mixture is stirred at 23 C for 17 hours, poured into water (100 cm3) and extracted with diethyl ether (5¡Á50 cm3). The combined organic layer is washed with water (50 cm3), brine (50 cm3) and dried over anhydrous magnesium sulfate then filtered. The filtrate is concentrated in vacuo to obtain an oily residue. The crude is purified using silica gel column chromatography (40-60 petroleum) to obtain an oily residue. The resulting oil is triturated with methanol to form a fine cream precipitate, which was filtered and washed well with methanol to give 1,4-dibromo-2,5-bis-trimethylsilanylethynyl-benzene (11 g, 84%) as a cream solid.

According to the analysis of related databases, 63262-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; Mitchell, William; D’Lavari, Mansoor; Wang, Changsheng; Tierney, Steven; Song, Jingyao; (75 pag.)KR2015/16254; (2015); 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

In a nitrogen-purged four-necked flask, 2-iodo-4-nitroaniline(5.11 g, 19.4 mmol), Bis(triphenylphosphine)palladium(II) dichloride (281.7 mg, 0.401 mmol), Copper iodide (160.7 mg, 0.844 mmol),And 30 ml of diethylamine, and the mixture was stirred at room temperature (20 C.) for 10 minutes.Thereafter, N-Boc-propargylamine (3.72 g, 24.0 mmol) was added and the mixture was stirred at room temperature (20 C.) for 4 hours. After disappearance of the raw material was confirmed by HPLC (high performance liquid chromatography), 200 ml of ethyl acetate and 200 ml of 1 M ammonium chloride aqueous solution were added and extracted. The obtained organic layer was washed twice with 1 M ammonium chloride aqueous solution and dried over anhydrous magnesium sulfate. After removing the drying agent, the filtrate was concentrated and purified by silica gel column chromatography (distillate: ethyl acetate: hexane = 3: 7 (volume ratio)). The yield was 4.97 g, and the yield was 88.0%.

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 LIMITED; SAKUMOTO, NAOKI; (63 pag.)JP5846230; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com