Category: iodides-buliding-blocks

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. 618-91-7, name is Methyl 3-iodobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-iodobenzoate

3-iodo-benzoic acid methyl ester (1g, 3.82mmol), piperidine (0.76 ml, 7 . 63mmol), potassium carbonate (2.11g, 15 . 26mmol), cuprous iodide (0.15g, 0 . 76mmol), L-proline (0.18g, 1 . 53mmol)-miscible in 20mlDMSO in, under the protection of nitrogen heating 60 C reaction 8h, water 200 ml dilution, using ethyl acetate (30 ml ¡Á 3) extraction, combined with the phase, to saturated salt water (15 ml ¡Á 2) washing, dry anhydrous sodium sulfate, filtered, the filtrate may be amber oily evaporating solvent under reduced pressure, column chromatography (petroleum ether/ethyl acetate, 95:5, v/v) purified VI-10.61g colorless oily, yield 84%.

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; CHINA PHARMACEUTICAL UNIVERSITY; HUANG, WENLONG; QIAN, HAI; LI, ZHENG; YANG, JIANYONG; SU, XIN; PAN, MIAOBO; (18 pag.)CN105566263; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 82998-57-0, 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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-iodo-4-methylbenzoic acid 5-1 (262mg, 1.0mmol) in dry DCM (10mL) at 0C was added oxalyl chloride (0.13mL, 1.5mmol) and 3 drops of dry DMF. The resulting reaction mixture was stirred at room temperature for 3h, and then the solvent was removed under reduced pressure. The crude product was used directly for the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 3-Iodo-4-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Yang; Peng, Xia; Guan, Xiaocong; Lu, Dong; Xi, Yong; Jin, Shiyu; Chen, Hui; Zeng, Limin; Ai, Jing; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 122 – 132;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 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.

To a stirred solution of 18-2B (3.2 g, 11.5 mmol; TCI) in THF was treated with isopropyl magnesium chloride (/-PrMgCl) in THF (22.8 mL of 2.0 M in THF, 46 mmol) at -15 C. After 2 hr stirring at the same temperature, dry DMF (4.3 mL, 57.5 mmol) was added and the reaction was allowed to warm to 23 C over 1 hr. After consumption of the starting material (by TLC), the reaction was quenched with aqueous 1M HC1 (60 mL), followed by extracted with EtOAc, dried over Na2S04 and concentrated. The crude compound was purified by flash column chromatography (100-200 silica) using 5% EtOAc in hexanes to afford 18-3B (1.4 g, 7.8 mmol, 70% yield) as an off-white solid. MS (ESI): m z 179.2 (M+l)+.

According to the analysis of related databases, 5471-81-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina C.; FEESE, Michael D.; LEE, Sam S.; (169 pag.)WO2016/154241; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 640280-28-0,Some common heterocyclic compound, 640280-28-0, name is 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF3I, 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.

Cs2CO3 (926 mg, 2.84 [MMOL),] Pd2 (dba) 3 (104 mg, 0.114 mmol), [2-DICYCLOHEXYLPHOSPHINO-2′-] (N, N-dimethylamino) biphenyl (36 mg, 0.091 mmol), anhydrous toluene (5 mL), methyl 2- amino-5-cyanobenzoate [PHA-522499] (200 mg, 1.136 mmol), 1-iodo-2-bromo-5- trifluoromethylbenzene [PHA-738728] (400 mg, 1.136 [MMOL).] The mixture is heated at [65 C] for 66 h. The resulting mixture is cooled to room temperature and filtered through [CELITE (E).] The filtrate is concentrated and purified by flash chromatography. The yield is 65mg of methyl 5-cyano-2-{[2-{[4-cyano-2-(methoxycarbonyl) phenyl] amino}-4- (trifluoromethyl) phenyl] amino} benzoate, 13%. MS (ESI-) for [C25HI7F3N404] [NT/Z] 493 (M-H)-. ‘H NMR (400 MHz, CDCl3) 8 9.93 (bs, [1] H), 9.83 (bs, [1] H), 8.22 [(M,] 2 H), 7.69 (bs, [1] H), 7.52 [(M,] 4 H), 7.05 (m, [1] H), 6.81 (m, [1] H), 3.84 (s, 3 H), 3.86 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; PHARMACIA ITALIA S.P.A; WO2004/2940; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 618-91-7, 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. 618-91-7, name is Methyl 3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Obtained in Step 1 3-iodobenzoic acid methylester (104) and (3.04 g) was dissolved in THF (24 mL), PdCl2 (PPh3) 2 (244 mg), CuI (133 mg), triethylamine (. 6 mL ), was added trimethylsilylacetylene (1.37 g), under an argon atmosphere and stirred at room temperature for 26 hours. Thereaction mixture was filtered, the filtrate was concentrated, the residue was purified by silica gel flash column chromatography(developing solvent n-hexane:ethyl acetate = 50: 1) to give the title compound (2.42 g, 90% yield) white It was obtained as asolid.

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 3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nagoya City University; Miyata, Naoki; Suzuki, Takayoshi; Ota, Yosuke; Ueda, Ryuzo; Ida, Shinsuke; Rie, Masaki; (47 pag.)JP5725475; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, 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 199786-58-8, SDS of cas: 199786-58-8

A solution of oxalyl chloride (1 .99 mL, 23.04 mmol, 1 .6 equiv) in DCM (25 mL) was cooled to -70C and DMSO (2.44 mL, 34.5 mmol, 2.4 equiv) in DCM (25 mL) was added at -65C to -70C. The reaction mixture stirred for 10 minutes under nitrogen atmosphere at – 70C and then (5-bromo-2-iodophenyl)methanol (4.55 g, 14.4 mmol, 1 .0 equiv) in DCM (100 mL) was added. The reaction mixture was stirred at -65C for 15 minutes and triethylamine (10 mL, 72 mmol, 5.0 equiv) was added. The reaction mixture was allowed to warm to -10C and stir for 1 h. Water (40 mL) was added and the reaction mixture was allowed to warm to room temperature. The organic layer was separated and evaporated to obtain 5-bromo-2-iodobenzaldehyde (4.2 g, 93 %) as white solid. 1H NMR (400 MHz.CDCb) delta ppm 7.45 (d, J=7.6 Hz, 1 H), 7.81 (d, J=1 1 .6 Hz, 1 H), 7.98 (d, J=1 .6 Hz, 1 H), 9.97 (s, 1 H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, 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. HPLC of Formula: C8H8BrI

5.5 g (17.8 mmol) 2-Bromo-5-iodo-1 ,3-dimethylbenzene, 6.5 g (12.7 mmol) EG1 , 366 mg (0.3 mmol) tetrakis(triphenylphosphin)-palladium(0) and 2.7 g (13 mmol) sodium carbonate are dissolved in 200 ml toluene, ethanol and water (2:1 :1 ) and stirred for 16 hours at 90 C. After cooling down to room temperature 100 ml toluene are added, the organic phase is separated and washed with water (2×50 ml). The organic phase is concentrated to dryness under reduced pressure. The residue is purified by recrystallization from toluene/heptane. Yield: 6.2 g (11 mmol; 86 %)

The synthetic route of 2-Bromo-5-iodo-1,3-dimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; LINGE, Rouven; MEYER, Sebastian; LACKNER, Aaron; HEIL, Holger; KOENEN, Nils; (168 pag.)WO2019/101833; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 175278-30-5, name is 4-Bromo-2-ethyl-1-iodobenzene, 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 175278-30-5, Application In Synthesis of 4-Bromo-2-ethyl-1-iodobenzene

Example 6 : Preparation of 2-r4-(4-chlorophenoxy)-2-ethylphenyl1cvclopentane-1 ,3-dioneStep 1 : Preparation of (4-bromo-2-ethylphenyl)furan-2-yl methanolMagnesium turnings (1.16g, 0.048mol) are stirred under a nitrogen atmopsphere for 30 minutes, followed by dropwise addition of 4-bromo-2-ethyl-1-iodobenzene (15.Og, 0.048mol) as a solution in anhydrous tetrahydrofuran (40ml), until the magnesium is just covered. A crystal of iodine is added and the reaction heated to reflux. After initiation begins external heating is stopped and the remaining aryl halide solution is added at such a rate as to maintain a controlled reflux. Once addition is complete the reaction is heated at reflux for 1 hour and the mixture is then cooled to room temperature. A solution of furan-2-carbaldehyde (4.0ml, 0.048mol) in anhydrous tetrahydrofuran (10ml) is then added dropwise, and the suspension is then stirred at room temperature for 20 hours. The reaction is quenched with saturated ammonium chloride (200ml) and extracted with ethyl acetate (200ml). The organic phase is separated, dried over anhydrous magnesium sulfate then evaporated under reduced pressure. The crude product is purified by flash column chromatography (1 :4 ethyl acetate/hexane eluant) to afford (4-bromo-2-ethyl- phenyl)furan-2-yl methanol as a brown oil.

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; SYNGENTA LIMITED; MATHEWS, Christopher John; FINNEY, John; SCUTT, James Nicholas; ROBINSON, Louisa; DELANEY, John Stephen; WO2010/89210; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, name is 1,2-Difluoro-4-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1,2-Difluoro-4-iodobenzene

A mixture of methyl indole-5-carboxylate 24a (2 g, 11.4 mmol), 1-iodo-3,4-difluoro-benzene 24b (1.5 mL, 12.5 mmol), CuI (0.22 g, 1.14 mmol), trans-N,N’-dimethylcyclohexane-1,2-diamine (0.54 mL, 3.43 mmol), and K3PO4 (6.06 g, 28.5 mmol) in toluene (12 mL) was heated at 110 C. for 7 hours. The reaction mixture was diluted with CH2Cl2 and filtered. The solution was concentrated and the residue was purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give 24c (3.0 g).

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Connolly, Peter J.; Macielag, Mark J.; McDonnell, Mark E.; Zhu, Bin; US2012/77797; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16355-92-3, 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. 16355-92-3, name is 1,10-Diiododecane, This compound has unique chemical properties. The synthetic route is as follows.

(3) Dissolve 2-methyl-4-aminoquinoline (4.75 g, 0.03 mol) in 100 mL of sulfolane, add 1,10-diiododecane (3.94 g, 0.01 mol), and raise the temperature to 80C to react 12h, lower the temperature, filter, wash the filter cake twice with water, wash the filter cake once with methanol, dry diquindine 8g, yield 56.7%, HPLC purity 81.5%;

The chemical industry reduces the impact on the environment during synthesis 1,10-Diiododecane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wuhan Zhidun Science And Technology Co., Ltd.; Li Yaping; Xie Honglei; Zhang Ruipeng; Zhang Yixing; (8 pag.)CN111018777; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com