Month: November 2020

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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64248-58-4

General procedure: General procedure for the synthesis of alpha-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33-48h. The cooled mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired alpha-arylacetic acid tert-butyl esters.

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

Reference:
Conference Paper; Zhao, Duo; Jiang, Yongwen; Ma, Dawei; Tetrahedron; vol. 70; 20; (2014); p. 3327 – 3332;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

General procedure: To a solution of NCTD (1, 1.0 g, 5.95 mmol) dissolved in tetrahydrofuran (THF, 10 mL)accompanied by triethylamine (TEA, 0.5 mL) as the acid-binding agent was added the correspondingaromatic amine (1 equiv., 5.95 mmol). When the reaction was complete after 14 h as checkedby TLC analysis, the solution was concentrated under reduced pressure and diluted with acetone(100 mL). The resulting filter cake was either recrystallized from methanol or purified by columnchromatography (MeOH/CH2Cl2, 1: 4, v/v) to afford the desired products II (1-36). The yields,physical properties, 1H-NMR, 13C-NMR, and HRMS-ESI of the target compounds II were as follows.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yang; Sun, Wenbo; Zha, Shunqing; Wang, Huan; Zhang, Yalin; McPhee, Derek J.; Molecules; vol. 20; 12; (2015); p. 21464 – 21480;,
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. 627-32-7 name is 3-Iodo-1-propanol, 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. 627-32-7

Mitragynine (50.0 mg, 0.126 mmol) was dissolved in 3-iodopropanol (0.33 mL), and acetonitrile (CH3CN, 0.5 mL) was added to the solution. Under ice cooling, IBDA (40.5 mg, 0.126 mmol) was added in four portions at intervals of 4 minutes, and the mixture was stirred at room temperature for 1 hour in an argon atmosphere. The reaction liquid was poured into an ice-cold saturated sodium bicarbonate aqueous solution and extracted three times with ether. The extracted organic layers were washed with brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure and vacuum drying. Thus, a residue was obtained. The resultant residue was purified by medium pressure liquid chromatography (aminosilica gel, 30% ethyl acetate/n-hexane) to obtain an iodinated form represented by the following formula (V) (31.9 mg, 46% yield).Analysis data of the product are shown below. 1H-NMR (400 MHz, CDCl3) delta [ppm]: 7.45 (1H, s, H-17), 7.32 (1H, dd, J=8.0, 8.0 Hz, H-11), 7.24 (1H, d, J=7.6 Hz, H-12), 6.75 (1H, d, J=8.1 Hz, H-10), 3.87 (3H, s, 9-OCH3), 3.81 (3H, s, 17-OCH3), 3.71 (3H, s, 22-OCH3), 3.29 (2H, m, H2-1?), 3.05-2.98 (3H, overlapped, H-3, H-5, and H-15), 2.93 (2H, dd, J=5.3, 5.3 Hz, H2-3?), 2.89-2.70 (3H, overlapped, H-6, H-14, and H-21), 2.59 (1H, m, H-5), 2.45 (1H, dd, J=11.2, 2.6 Hz, H-21), 2.08-1.88 (3H, overlapped, H-14 and H2-2?), 1.74-1.56 (3H, overlapped, H-6, H-19, and H-20), 1.23 (1H, m, H-19), 0.82 (3H, dd, J=7.2, 7.2 Hz, H3-18).13C-NMR (100 MHz, CDCl3) delta [ppm]: 184.0 (C-2), 169.3 (C-22), 160.7 (C-17), 156.5 (C-9), 155.5 (C-13), 130.9 (C-11), 123.0 (C-8), 114.3 (C-12), 111.2 (C-16), 108.8 (C-10), 86.1 (C-7), 63.2 (C-1?), 62.2 (17-OCH3), 61.8 (C-3), 58.1 (C-21), 55.4 (9-OCH3), 51.3 (22-OCH3), 50.3 (C-5), 40.5 (C-20), 39.3 (C-15), 35.2 (C-6), 33.7 (C-2?), 25.9 (C-14), 18.9 (C-19), 12.8 (C-18), 3.7 (C-3?).UV (MeOH) lambdamax: 301.0, 245.5 (sh), 221.5 nm.CD (0.151 mM, MeOH, 24 C.), lambda nm (De): 345 (0), 309 (+2.8), 290 (0), 281 (-0.8), 275 (0), 258 (+4.8), 242 (0), 221 (-9.4), 210 (0). EI-MS (%) m/z: 582 (M+, 41), 397 (100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; NATIONAL UNIVERSITY CORPORATION CHIBA UNIVERSITY; TAKAYAMA, Hiromitsu; (11 pag.)US2016/340352; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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. 660-49-1.

Production Example 342 benzhydrylidene-(3-fluoro-5-iodophenyl)-amine 0.75 g of the title compound (yellow oil) was obtained from 3.2 g of 3-fluoro-5-iodophenylamine (compound in Production Example 341) by the same reaction as in Production Example 336.1H-NMR (CDCl3) delta: 6.36-6.43(m, 1H), 6.86-6.92(m, 1H), 6.96-7.02(m, 1H), 7.08-7.16(m, 2H), 7.28-7.54(m, 6H), 7.68-7.76(m, 2H)

The synthetic route of 3-Fluoro-5-iodoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Under N2, a suspension of methyl 2-amino-5-iodobenzoate (4) (2.77 g, 10 mmol), Pd(PPh3)4 (1.159 mg, 1 mmol), CuI (381 mg, 2 mmol), Et3N (4.2 mL, 30 mmol) and propargyl alcohol (1.75 ml, 30 mmol) in DMF (20 mL) was stirred at rt for 15 h. TLC analysis (petrol ether: ethyl acetate 1:1) indicated the fully consumption of starting material. The reaction was quenched with 200 ml sat. NaCl solution. Ethyl acetate: petrol ether 1:1 (200 ml) was added to the mixture and the aqueous layer was extracted with ethyl acetate:petrol ether 1:1 three times. After drying the combined organics over MgSO4, the solution was concentrated and purified by silica gel chromatography (petrol ether:ethyl acetate 80:20 to ethyl acetate), giving Compound 5 as a yellow oil (1.88 g, 92%). 1H NMR (CDCl3) delta 3.78 (s, 3H), 4.25 (s, 2H, CCH?2), 7.27-7.36 (m, 2H, arom.H), 7.58-7.65 (m, 1H, arom.H).

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 77317-55-6.

Reference:
Patent; Illumina, Inc.; Illumina Cambridge Limited; Wu, Xiaolin; Smith, Randall; Shieh, Peyton; Beierle, John M.; George, Wayne N.; Lawrence, Elliot John; Mao, Jie; Liu, Xiaohai; (62 pag.)US2019/352327; (2019); A1;,
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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3032-81-3

A 1000-mL flask equipped with overhead stirrer, condenser and thermometer was charged with l,3-dichloro-5-iodobenzene (99.0 g, 0.36 mol), 1,3-dimethyl 2-(3,5- dichlorophenyl)propanedioate (91.0 g, 0.69 mol), copper(I) iodide (4.0 g, 0.021mol), 2-picolinic acid (5.2 g, 0.042 mol) and cesium carbonate (350 g, 1.07 mol) in 1,4-dioxane (600 mL). The reaction mixture was heated under nitrogen to 90 C for 3 hours. The mixture was then cooled to 30 C, diluted with water (300 mL) and hexane (200 mL), and partitioned. The organic phase was washed with saturated aqueous ammonium chloride solution (200 mL) and concentrated under vacuum to a viscous oil. The resulting material was used directly in the next step.

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; E. I. DU PONT DE NEMOURS AND COMPANY; HOFFMANN, Christian; ZHANG, Wenming; CHEN, Yuzhong; WO2013/192035; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

55406-53-6, A common heterocyclic compound, 55406-53-6, name is 3-Iodoprop-2-yn-1-yl butylcarbamate, molecular formula is C8H12INO2, 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.

EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of IPBC was determined by means of HPLC at the beginning and after two weeks.

The synthetic route of 55406-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uhr, Hermann; US2009/36555; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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. 612-55-5

General procedure: An aryl iodide (2′: 0.20 mmol) in a 20 mL Schlenk tube was added successively toluene (1.5 mL), a THF solution of an arylmagnesium bromide (1: 0.30 mmol) and THF (overall 0.50 mL), and the resulting mixture was stirred at 80 C for 24 h. After cooling, the reaction mixture was quenched with a 1 N HCl aqueous solution (1.0 mL) and extracted with Et2O (10 mL x 3). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel chromatography (hexane orhexane/diethyl ether, PTLC) to give the corresponding coupling product (3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 612-55-5, its application will become more common.

Reference:
Article; Shirakawa, Eiji; Okura, Keisho; Uchiyama, Nanase; Murakami, Takuya; Hayashi, Tamio; Chemistry Letters; vol. 43; 6; (2014); p. 922 – 924;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 116632-39-4, name is 5-Bromo-2-iodotoluene, I believe this compound will play a more active role in future production and life. 116632-39-4

Ethyl 4-pyrazolecarboxylate (202 mg, 1.44 mmol), 5-bromo-2-iodotoluene (0.20 mL, 1.4 mmol), (15,25,N7E,N2i^-N7,N2-bis(pyridin-2-ylmethylene)cyclohexane-l,2-diamine (84 mg, 0.29 mmol), Copper(I) oxide (10 mg, 0.072 mmol), and cesium carbonate (939 mg, 2.88 mmol) were combined in a 5 mL microwave vial and dissolved in acetonitrile (3.0 mL). The reaction was stirred at 82C overnight. The reaction was then filtered through Celite rinsing with ethyl acetate. The solution was concentrated in vacuo and purified by silica chromatography, eluting with 10-25% ethyl acetate in hexanes to give ethyl l-(4-bromo-2-methylphenyl)-lH- pyrazole-4-carboxylate.LRMS (ESI) calc’d for Ci3Hi4BrN202 [M+H]+: 309, found 309.

The chemical industry reduces the impact on the environment during synthesis 116632-39-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, A common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, molecular formula is C2H5IO, 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.

Compound 4a (617 mg, 4.6 mmol) was reacted with 2-Iodoethanol (0.54 mls, 6.9 mmol) and diisopropylethylamine (1.2 mls, 6.9 mmol) in ACN (20 mls) at 30 C. for 48 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane and EtOAc to provide the intermediate 4b (483 mg, 2.7 mmol, 59% yield) as a light brown oil. HRMS (ESI, positive) m/z calcd. for C11H18N1O1 [M+H]+: 180.13829, found: 180.13829. 1H NMR (400 MHz, CDCl3) delta 7.28-7.19 (t, J=8.0 Hz, 2H), 6.92-6.85 (d, J=8.2 Hz, 2H), 6.83-6.75 (t, J=7.3 Hz, 1H), 4.03-3.88 (hept, J=6.6 Hz, 1H), 3.70-3.62 (t, J=6.2 Hz, 2H), 3.34-3.24 (m, 2H), 1.19-1.12 (d, J=6.6 Hz, 6H).

The synthetic route of 2-Iodoethanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CINCINNATI CHILDREN’S HOSPITAL MEDICAL CENTER; UNIVERSITY OF CINCINNATI; Merino, Edward J.; Mulloy, James C.; Li, Guorui; Bell-Horwath, Tiffany; US2013/230542; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com