Month: December 2020

619-58-9, name is 4-Iodobenzoic acid, 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. 619-58-9

General procedure: A 20mL Schlenk tube with a magnetic stir bar was charged with aryl halide (2mmol), arylboronic acid (2.4mmol), K2CO3 (5mmol), 10mL of solvent [H2O, H2O-MeOH (1:1), H2O-EtOH (1:1), H2O-EG (1:1)] and an aliquot of 0.01M solution of palladium complexes PdCl2(L)2 or Pd[(L)4]Cl2 in MeOH (0.001-0.2mol%) under air atmosphere. The reaction mixture was placed in a preheated oil bath: at 100C for MeOH-H2O, at 110C for EtOH-H2O, at 140C for H2O and at 160C for EG-H2O; and stirred under reflux for the given time. After this time, the mixture was cooled, acidified by 5M HCl (in the case of acids) and diluted with 10mL of H2O and 10mL of Et2O (or EtOAc). The organic phase was separated, and the aqueous layer was extracted with Et2O EtOAc) (2¡Á10mL). The combined organic layers were washed with H2O (10mL), brine (10mL), and dried over Na2SO4. The pure products were obtained by a simple filtration of ether solution through silica gel pad and evaporation of a solvent.

Statistics shows that 619-58-9 is playing an increasingly important role. we look forward to future research findings about 4-Iodobenzoic acid.

Reference:
Article; Bumagin, Nikolay A.; Catalysis Communications; vol. 79; (2016); p. 17 – 20;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene, This compound has unique chemical properties. The synthetic route is 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.

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; 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

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. 3268-21-1 name is 1,4-Diiodo-2,3,5,6-tetramethylbenzene, 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. 3268-21-1

The Suzuki coupling reaction of 4-bromo-2-phenylpyridine (I) with N-Boc-2-pyrroleboronic acid, using Pd(OAc)2 as the catalyst, was carried out in a glove box due to the air sensitivity of PtBu3, and afforded 4-bromo-2-(N-Boc-pyrrol-2-yl)pyridine (6) with good selectivity. This allowed the remaining Ar-Br bond to be utilised and converted into a boronic ester functional group (7) and mono-Suzuki coupled to 1,4-diiododurene to yield compound (8). The cross-linking group was attached to compound (8) via Suzuki coupling reaction with (4-(non-8-en-1-yloxy)phenyl)boronic acid to yield compound (9). Boc deprotection to give (10) and subsequent cyclometalation using lrCl3.3H20 in 2-ethoxyethanol/H20 at 110 C afforded DIM ER-2 that was converted to the cross-linkable bis-heteroleptic acac phosphor Ir(4- durph-2-pyrpy)2(acac) using acetylacetone and sodium carbonate in 2-ethoxyethanol at 9000.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Diiodo-2,3,5,6-tetramethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; LOMOX LIMITED; JUDD, Luke; ALDRED, Matthew; KOCH, Gene C.; (71 pag.)WO2018/162880; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, The chemical industry reduces the impact on the environment during synthesis 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried screw cap test tube was charged with a magnetic stir bar, Pd(PPh3)2Cl2 (2 mol%), CuI (4 mol%), and K2CO3 (0.4mmol). The tube was then evacuated and backfilled with argon.The evacuated/backfill sequence was repeated two additional times. Under a counter-flow of argon, DMF (1 mL), iodoarene(1a, 0.2 mmol), and methyl propiolate (2a, 0.3 mmol) were added. The tube was placed in a preheated oil bath at 80 C, andthe mixture was stirred vigorously for 10 min. Then the screwcap was opened and 2-pyridyl ethyl ester (3a, 0.2 mmol) wasadded in air at 80 C. The mixture was allowed to react for another 8 h at 80 C in air atmosphere. After the reaction was finished, water (5 mL) was added, and the solution wasextracted with ethyl acetate (3 ¡Á 5 mL), the combined extractwas dried with anhydrous MgSO4. Solvent was removed, andthe residue was separated by column chromatography (petroleumether/ethyl acetate, 2:1) to give 4a (50 mg, 86%) as ayellow solid.

The chemical industry reduces the impact on the environment during synthesis 1,2-Difluoro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Zhengwang; Liu, Tanggao; Ma, Xiaoyue; Liang, Pei; Long, Lipeng; Ye, Min; Synlett; vol. 30; 7; (2019); p. 863 – 867;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, A common compound: 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, 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.

General procedure: Indole (1.0 mmol),Cs2CO3 (1.0 mmol), 2-bromopyridine (1.5 mmol), Cu2O (0.1 mmol), and DMA (3 mL) were added to a 5-mL vial. The vial was sealed with a crimp cap and placed in a Biotage initiator microwave cavity. After irradiation at 200C for the appropriate time and subsequent cooling, the reaction mixture was diluted with saturated aqueous ammonium chloride. Products were isolated by extraction into ethylacetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. Products were purified by silica gel column chromatography using a hexane:ethyl acetate solvent. N-2-pyridylindole (2a) was obtained (80% yield) as yellow oil;

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, 1,2-Difluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kwon, Jae-Kwan; Lee, Jin -Hee; Kim, Tae Sung; Yum, Eul Kgun; Park, Hee Jung; Bulletin of the Korean Chemical Society; vol. 37; 12; (2016); p. 1927 – 1933;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

General procedure: A 10mL-sealed tube was charged with aryl iodides or bromides (1mmol), CuI (19mg, 0.1mmol) in NH4OH (1.5mL, 27% NH3 in H2O) and PEG300 (0.5g). The tube was flushed with Ar gas before being capped. The solution was stirred for the given times at 130C or 110C. The resulting suspension was cooled to room temperature and saturated aqueous Na2SO4 solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL¡Á3). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (hexanes/EtOAc=5/1?1/2 or EtOAc) to give the desired primary arylamines.

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

Reference:
Article; Jung, Hee Seon; Yun, Taeil; Cho, Yungyeong; Jeon, Heung Bae; Tetrahedron; vol. 72; 40; (2016); p. 5988 – 5993;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 62720-29-0, name is 1,3-Dibromo-5-fluoro-2-iodobenzene, 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. 62720-29-0

A solution of l,3-dibromo-5-fluoro-2-iodobenzene (50 g, 132 mmol ) in anhydrous toluene (300 mL) cooled to -35 C was added the solution of isopropylmagnesium chloride (84 mL, 171 mmol, 2.0 M in diethyl ether ) over a period of 30 minutes while maintaining the internal temperature below -25C. A clear brown solution was obtained. Stirring was continued for 1.5 h. Then anhydrous DMF (34 mL, 436 mmol ) was added over a period of 30 minutes. The temperature of the reaction mixture increased to -19C. The reaction mixture was warmed to 10C (room temper-ature) over lh and stirred at this temperature for 1.5 h. The reaction was quenched with saturated aqueous NH4C1 (100 mL), filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate: from 50: 1 to 20: 1) to give 197a ( 20 g, yield 54%) as a yellow solid.

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 62720-29-0.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., 624-75-9

Step 2: Synthesis of 2-(2-chloro-6-morpholino-9H-purin-9-yl)acetonitrile (14c)To a solution of 13a (1.18 g, 4.94 mmol) in acetonitrile/DMSO (19:1) was added 2- iodoacetonitrile (0.71 mL, 9.87 mmol) and K2C03 (1.36 g, 9.87 mmol). The resulting mixture was heated at 60CC for 3 h. Then the solvents were removed in vacuo and water was added. The aqueous layer was extracted with DCM (x2) and the combined organic layers was washed with brine (xl), dried over MgSO4 and evaporated in vacuo. The crude oil was purified by flash chromatography(silica, 50% ethyl acetate in hexanes) to afford 14c (1.31 g, 95%) as pale 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:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; WANG, Haishan; CHEN, Dizhong; SOH, Chang Kai; WO2015/137887; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

627-32-7,Some common heterocyclic compound, 627-32-7, name is 3-Iodo-1-propanol, molecular formula is C3H7IO, 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.

Cesium carbonate [(5.] 54 g) is added to a solution [OFN (4-CHLOROBENZYL)-4-HYDROXY 2-] (hydroxymethyl) thieno [2, [3-B]] [PYRIDINE-5-CARBOXAMIDE] (5.23 g, prepared as described in US 6,239, 142) and 2-(3-iodopropoxy)tetrahydro-2H-pyran (4.32 g, prepared by mixing equal molar amounts of 2-iodopropanol and 3, 4-dihydro-2H-pyran) in DMF (20 mL). The mixture is heated at [60 C] for 4 hours. The solvent is evaporated and the residue is dissolved in 10% [MEOH] in [CH2C12.] The mixture is washed with water and the organic layer is dried (MgSO4), filtered, and concentrated. The crude product is purified by column chromatography [(CH2CLJMETHANOL,] [95/5)] followed by recrystallization from EtOAc to afford 4.82 g of the title compound as white crystals. Physical characteristics. 1H NMR (400 [MHZ,] DMSO-d6) 8 10.55, 8.71, 7.39, 7.33, 7.29, 5.79, 4. [70,] 4.53, 4.49, 4. [38, 3.] 68,3. [37,] 2.11, 1.63, 1.53, 1.40 ; MS [(EI)] m/z 490 [(MF)] ; Anal. Found: C, 58.74 ; H, 5.66 ; N, 5.61.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-1-propanol, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; FLECK, Bruce, Francis; WO2004/22567; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

672-57-1, 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 672-57-1 as follows.

Three point eight (3.8) ml of n-butyllithium (2.6 M hexane solution) was added dropwise to a mixture of 3.00 gof 1-chloro-2-iodo-4-(trifluoromethyl)benzene and 15 ml of tetrahydrofuran at -70C, followed by stirring for 30 minutes.Thereafter, a mixture of 1.69 g of N-methoxy-N-methyltrifluoroacetamide and 5 ml of tetrahydrofuran was added dropwisethereto at -70C. Subsequently, after the reaction mixture was stirred for 1 hour at room temperature, water was addedthereto, and extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, driedover magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gelcolumn chromatography, thereby obtaining 1.66 g of 2,2,2-trifluoro-1-[2-chloro-5-(trifluoromethyl)phenyl]ethanone.

According to the analysis of related databases, 1-Chloro-2-iodo-4-(trifluoromethyl)benzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com