Month: July 2021

Reference of 2043-55-2, These common heterocyclic compound, 2043-55-2, name is 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane, 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.

Diethyl malonate (11.5 mL, 75.7 mmol) was added dropwise to an ice-cold suspension of sodium hydride (60percent dispersion in mineral oil, 2.21 g, 55.4 mmol) in THF (150 mL) at 0 °C during 15 min. The resulting mixture was stirred for 30 min while allowing the temperature from 0?23 °C. 1H,1H,2H,2H-nonafluorohexyl iodide (9.4 mL, 50.5 mmol) was added slowly to the reaction and the mixture was heated at reflux for 3 h, and then was cooled to 23 °C. Water (100 mL) and ethyl ether (100 mL)were added to it. The aqueous layer was extracted with ethyl ether (3 80 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography to afford diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (6) as a colorless liquid (18.2 g, 89 percent). 1H NMR (400 MHz, CDCl3): delta 4.30?4.17 (m, 4H), 3.44?3.40 (m, 1H), 2.23?2.13 (m, 4H), 1.30?1.26 (m, 6H). 19F NMR (CDCl3, 376 MHz): delta -81.98 (3F, tt, J1 = 11.2 Hz, J2 = 3.7 Hz), 115.37 (2F, quintet, J = 15.0 Hz), 125.33 to 125.36 (2F, m), 126.89 to 126.96 (2F, m). 13C NMR (100 MHz, CDCl3): delta 168.61, 61.90, 50.77, 28.46, 19.77, 14.06; ESI-MS (m/z): 429 [M+Na]+. Anal. Calcd. for C13H15F9O4: C, 38.44; H, 3.72. Found: C, 38.12; H, 3.87.

The synthetic route of 2043-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bodduri, V.D. Vijaykumar; Chirumarry, Sridhar; Lim, Jae-Min; Lee, Yong-Ill; Jang, Kiwan; Choi, Bong-In; Chung, Seon-Yong; Shin, Dong-Soo; Journal of Fluorine Chemistry; vol. 163; (2014); p. 42 – 45;,
Iodide – Wikipedia,
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Electric Literature of 90347-66-3, 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 90347-66-3 as follows.

A dry flask was charged with 3-iodo-4-methylbenzoic acid methyl ester (21.6 G, 78. 2 MMOL) and the flask was evaporated and then filled with argon and this process repeated twice. Dry THF (140 mL) was added, and the solution cooled to-50 C ; then isopropyl magnesium chloride (41 mL, 2.0 M in diethyl ether, 82 MMOL) was added slowly over 15 min keeping the temperature below-40 C. On completion of the addition the reaction mixture was stirred at-40 C for 45 min. A THF solution of ZnCl2 (10.78 G, 79.1 MMOL, 0.8 M) was added dropwise over 20 min. The reaction mixture was stirred at 0 C for 65 min; then 2-chloro-4-nitro-benzoyl chloride (17. 2 g, 78.2 MMOL) and TETRAKIS (TRIPHENYLPHOSPHINE) PALLADIUM (0) (4.03 g, 3. 49 MMOL) were added and the reaction mixture was allowed to warm to room temperature. After 4 h the reaction mixture was poured into a mixture of toluene/EtOAc/water, then shaken and separated. The aqueous phase was extracted with two more portions of EtOAc. The organic phases were combined, dried (MGS04), filtered, and concentrated in vacuo to afford the crude product. Crystallization from mixtures of ETOAC/PETROLEUM ether (40- 60) gave the title compound as yellow solid. The mother liquid was concentrated in vacuo and purified by chromatography using DCM as the eluent to give a second crop of the title compound.

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Iodo-3,5-bis(trifluoromethyl)benzene

Step K: Synthesis of ethyl 3,5-bis(trifluoromethyl)phenylphosphinate AZ3. To a degassed solution of 1-iodo-3,5-bistrifluoromethylbenzene (10.0 g, 29.4 mmol), anilinium hypophosphite (5.62 g, 35.3 mmol) and 3-aminopropyl triethoxysilane (7.81 g, 35.3 mmol) in anhydrous acetonitrile (200 mL) were added palladium acetate (132 mg, 0.588 mmol, 2 mol percent) and 1,3-bis(diphenylphosphino)propane (267 mg, 0.647 mol, 2.2 mol percent). The mixture was heated under reflux overnight, then cooled down to room temperature, diluted with ethyl acetate and hydrochloric acid (1 M), and partitioned. The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine, and dried over sodium sulfate. The volatiles were removed in vacuo, and the residue was purified by column chromatography using 30 to 70percent ethyl acetate in petroleum ether to afford compound AZ3 (4.65 g) as a cloudy oil in 52percent yield. 1H NMR (CDCl3, 400 MHz): delta 1.45 (t, J=7.1 Hz, 3H), 4.18-4.35 (m, 2H), 7.69 (d, J=579.6 Hz, 1H), 8.10 (s, 1H), 8.23 (s, 1H), 8.27 (s, 1H). 31P NMR (CDCl3, 161.8 MHz): delta 19.59 (J=580.6 Hz).

The synthetic route of 328-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2009/202480; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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. Computed Properties of C6H3ClFI

To a solution of 2-chloro-4-fluoro-l-iodo-benzene (3.6 g, 14.3 mmol) and 3-trifluoromethyl-lH-pyrazole (1.9 g, 14.4 mmol) in N,N-dimethylformamide (40 mL) was added potassium carbonate (2.4 g, 17.2 mmol), and the resulting mixture was heated at 135 C for 12 h. The reaction mixture was cooled to room temperature, poured in cold water (80 mL) and extracted with dichloromethane (2 x 40 mL). The combined organic extracts were dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with 10% ethyl acetate in hexanes to afford the title compound (4.2 g) as a white solid. lH NMR delta 10.4 (s, 1H), 7.88 (m, 2H), 7.80 (d, 1H), 7.27 (m, 1H), 6.68 (d, 1H). MS (AP+) 373 amu.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101335-11-9, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; REDDY, Ravisekhara, P.; CAMPBELL, Matthew, James; KAR, Moumita; DESAEGER, Johan, A., J.; WO2014/4064; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

191348-14-8, name is 2-Iodo-4-methoxyaniline, 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. Recommanded Product: 191348-14-8

General procedure: Step B: Pyridine (1.5 mmol) was added to the o-iodo derivative as prepared above (1 mmol) in DCM (5 mL) at 0 C under nitrogen atmosphere. To this was added methane/p-toluene sulfonyl chloride (1.2 mmol) slowly at 0 C. Then, the reaction mixture was stirred at room temperature for 5-6 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with ethyl acetate (30 mL), washed with 2N HCl solution (10 mL) followed by brine solution (20 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using ethyl acetate-hexane to give the desired product 2.

The synthetic route of 191348-14-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rambabu; Raja, Guttikonda; Yogi Sreenivas; Seerapu; Lalith Kumar; Deora, Girdhar Singh; Haldar, Devyani; Rao, M.V.Basaveswara; Pal, Manojit; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1351 – 1357;,
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 13194-68-8 as follows. Computed Properties of C7H8IN

To a solution of 4-iodo-2-methylaniline (4.0 g, 17 mmol) and Pd(dppf Cl2 (140 mg, 0.17 mmol) in THF (50 mL) was added isopropylmagnisium chloride (25.5 mL, 51.0 mmol) at -78 C and was reacted at reflux for 4 h. The reaction was quenched with a saturated solution of NH4C1, extracted with EtOAc, dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography to give the title Compound as a brown solid (320 mg).

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (528 pag.)WO2017/100662; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19094-48-5, name is 3,5-Diiodobenzoic acid, molecular formula is C7H4I2O2, 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. SDS of cas: 19094-48-5

Step 2: Methyl 3,5-diiodobenzoate (YZ-I-93) To a solution of 3,5-diiodobenzoic acid (6.8 g, 18.18 mmol) in methanol (200.0 ml) was added CH3SO3H (0.5 ml). The reaction mixture was heated to reflux. After refluxing for 7.5 hours, most of the methanol was removed. Then, water (200.0 ml) was added and a dark-brown solid was collected by filtration. The product was purified by silica gel column chromatography using hexanes/ethyl acetate (8:2) as eluent. The final pure white product was obtained in the amount of 4.2 g (59.2%) by recrystallization from methanol/water: 1H NMR (CDCl3): delta 8.29 (d, 2HBz, J=1.6 Hz), 8.20 (t, 1HBz, J=1.6 Hz), 3.90 (s, 3H, OCH3). 13C NMR (CDCl3): delta 163.97, 148.99, 137.56, 133.08, 94.32, 52.73.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19094-48-5, its application will become more common.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; US2010/331509; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 51628-12-7, 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. 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 94 Synthesis of N-{2-[4-(3-(3-pyridyl)-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-hydroxy-2-(8-hydroxy-2(1H)-quinolinon-5-yl)ethylamine (94) Compound 94: Formula (XI) where R11 is 3-pyridyl a.Synthesis of 4-iodophenethylamine 4-Iodophenylacetonitrile (4.80 g, 19.7 mmol) was dissolved in tetrahydrofuran (25 ML) under nitrogen, and 1.0 M borane in tetrahydrofuran (29.6 ML, 29.6 mmol) was added via syringe.The reaction was heated at reflux for 1 hour, then cooled in ice and the excess borane was quenched by the addition of methanol (100 ML).When hydrogen evolution ceased, the solvents were removed under reduced pressure.The residue was dissolved in tetrahydrofuran (25 ML) and 4N HCl in dioxane (6.0 ML, 24 mmol) was added, followed by ether (75 ML).The hydrochloride salt of 4-iodophenethylamine was collected on a Buchner funnel, washed with ether (2*50 ML) and dried under reduced pressure.To generate the free base, the solid was partitioned between dichloromethane (200 ML) and 1N NaOH (100 ML).The aqueous layer was extracted with dichloromethane (2*100 ML).The combined organic layers were dried (Na2SO4) and concentrated to give 4-iodophenethylamine (4.52 g) as a colorless 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, 2-(4-Iodophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 188815-32-9,Some common heterocyclic compound, 188815-32-9, name is 3-Bromo-5-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

INTERMEDIATE 9; 2′-Fluoro-5-formyl-N-isopropyl-4′-methylbiphenyl-3-carboxamide; Step A: Methyl 3-bromo-5-iodo-benzoate; Methanol (50 mL) was added into a solution of 3-bromo-5-iodo-benzoic acid (25 g) in 2MHCl/ether (100 mL). The reaction mixture was then stirred at room temperature for 18 hrs. The solution was dried down under reduced pressure. The residue was then re-dissolved in ethyl ether (300 mL). The ether solution was washed with sat. Na2CO3 (3×200 mL), and water (3×200 mL). The organic layer was dried with sodium sulfate and evaporated to dryness to give the crude product. The crude product was then purified through a short silica column (eluted with 20% EtOAc/hexane) to give pure compound by TLC.

The synthetic route of 188815-32-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/58298; (2009); 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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-1-iodo-2-nitrobenzene

(1) In the reaction flask, add naphthobenzofuran-6-boronic acid (100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) tetratriphenylphosphine palladium , 500mL of toluene, 200mL of ethanol, 200mL of water and 40g (300mmol) of potassium carbonate, react at 100 C for 8h; after the reaction is complete, stop the reaction; cool to room temperature, separate the organic phase, concentrate, silica gel column chromatography to obtain yellow powder M1;

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; Yantai Xianhua Chemical Technology Co., Ltd.; Xing Qifeng; Feng Peichuan; Chen Yue; Hu Lingfeng; Chen Yili; (24 pag.)CN110734446; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com