Month: July 2021

Electric Literature of 128140-82-9, The chemical industry reduces the impact on the environment during synthesis 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, I believe this compound will play a more active role in future production and life.

Step 1) 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 3-bromophenylacetylene (2.5 g, 21.5 mmol), TEA (9.57 g, 94.6 mmol, 13.2 mL), bis(triphenylphosphine)dichloropalladium(II) (603 mg, 0.86 mmol), and CuI (98 mg, 0.516 mmol) in DMF (26 mL) was added 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 2.4 g of a dark orange oil (component A) and 1.44 g of a dark red oil (component B). Flash chromatography of Component A (SiO2, Hexanes) and Component B (SiO2, Hexanes) separately yielded 3.2 g, 72%, of the title compound as a light peach oil. MS (+ESI): m/z 345 ([M+H]+). Step 1: 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) in DMF (26 mL) was added TEA (9.57 g, 13.2 mL, 94.6 mmol), PdCl2(PPh3)2 (603 mg, 0.86 mmol), CuI (98 mg, 0.516 mmol), and 3-ethynyltoluene (2.5 g, 2.78 mL, 0.90 mmol). The reaction mixture was stirred for 4 h then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice more with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 1.44 g of a dark red oil and 2.44 g of a dark orange oil. Both fractions were rechromatographed, separately, to provide 3.2 g, 72%, of the title compound as a light peach oil. 1H NMR 500 MHz (CDCl3) delta 2.33 (s, 3H); 6.50 (t, J=73.6 Hz, 1H); 7.06 (d, J=8.81 Hz, 2H); 7.12 (d, J=6.83 Hz, 1H); 7.20 (d, J=7.53 Hz, 1H); 7.30 (d, J=7.76 Hz, 1H); 7.33 (s, 1H); 7.47-7.51 (m, 2H)

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-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (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. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Methyl 4-formyl-3-methylbenzoate (1616-18a). To a solution of methyl 4-iodo-3- methylbenzoate (1.0 g, 3.6 mmol) in THF (24 mL, 0.15 M) at -15C was added isopropylmagnesium chloride (7.2 ml, 14.5 mmol, 4.0 equiv). The reaction mixture was allowed to continue stirring at -15C for 2 hrs before N,N-dimethylformamide (1.4 ml, 18mmol, 5.0 equiv) was added. The mixture was warmed to room temperature over a period of 1 hr. At this time the reaction was quenched with HC1 and extracted with EtOAc (3x). The combined organic layers were washed with brine and dried over MgSO4, filtered and concentrated in vacuo.Purification was achieved using flash column chromatography on Si02 (Hexanes/EtOAc:6/1) to yield a white solid (0.45 g, 70 %) which was taken on without further purification.

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; EMORY UNIVERSITY; TRAYNELIS, Stephen F.; MULLASSERIL, Praseeda; GARNIER, Ethel C.; LIOTTA, Dennis C; ZIMMERMAN, Sommer; WO2014/25942; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 90347-66-3,Some common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, molecular formula is C9H9IO2, 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.

3-iodo-4-methylbenzoic acid. Methyl-3-Iodo-4-methylbenzoate (3 g, 109 mmol, 1 eq) dissolved in MeOH (30 ml) was added sodium hydroxide (1.3 g, 327 mmol, 3 eq) followed by the addition of water (15 ml). The above solution was stirred at room temperature for 14 h. The solution was concentrated under vacuum, and then added water. The pH of the reaction was bought to 3 using Cone. HCl. The solid obtained was filtered and dried under vacuum, Yield: 2.7 g (96 %). 1HNMR (400MHz, DMSO-d6): delta 2.44 (s, 3H), 7.45 (d, 7- 8.00 Hz ,1H), 7.85 (d, J= 3.18 Hz, IH), 8.31 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-iodo-4-methylbenzoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John F.; BENDER, John A.; BENO, Brett R.; GRANT-YOUNG, Katharine A.; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle E.; YEUNG, Kap-Sun; CHUPAK, Louis S.; WO2010/30538; (2010); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 191348-14-8, name is 2-Iodo-4-methoxyaniline, 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 191348-14-8, category: iodides-buliding-blocks

To a solution of 2-iodo-4-methoxyaniline 30-d ( 1.00 g, 4.02 mmol) in DMF cooled to 0C were sequentially added diethylamine (41 uL, 4.02 mmol), copper(I) iodide ( 143 mg, 0.80 mmol) and dichlorobis(triphenylphosphine) palladium (II) (282 mg, 0.40 mmol). After complete dissolution of copper(I)iodide, propyl 3,3-dimethylhex-5- ynoate 1 1 -d (805 mg, 4.42 mmol) was added dropwise at 0 C and the reaction was then stirred at room temperature overnight. Water and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride and brine, dried over anhydrous MgS04, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 30-e as a beige oil. MS (m/z) M+H=3()4.4

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-Iodo-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AEGERA THERAPEUTICS INC.; BUREAU, Patrick; FOURNIER, Jean-Hugues; JAQUITH, James, B.; LAURENT, Alain; ROSE, Yannick; PROULX, Melanie; WO2011/35417; (2011); 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8INO2

4-Amino-3-iodo-iV,./V-dimethylbenzamide < To a stirred solution of dimethylamine (9.0 mL, 135 mmol) in THF at O0C was added trimethylaluminium (50 mL, 2.0M solution in toluene, 100 mmol). The resulting solution was stirred at 00C for 10 minutes before addition of a solution of methyl 4- amino-3-iodobenzoate (19 g, 70 mmol) in THF (50 mL). The solution was heated to reflux for 1.5 h then allowed to cool to r.t before being poured onto ice (100 g). The resulting suspension was treated with aqueous 2M NaOH solution (100 mL) and partitioned with diisopropyl ether (2 x 100 mL). The combined organics were passed through a phase separator and concentrated to give the title compound (20 g, 96%) as a pale yellow oil which was used without further purification. 5H (CDCl3) 7.79 (IH, d, J 1.5 Hz), 7.29-7.26 (IH, m), 6.72 (IH, d, J8.2 Hz), 4.31 (2H, br. s), 3.07 (6H, s). LCMS (ES+) 261 (M+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 19718-49-1.

Reference:
Patent; UCB PHARMA S.A.; WO2009/71888; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 216393-67-8,Some common heterocyclic compound, 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, molecular formula is C6H4ClFIN, 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 65 – PREPARATION of A/-(2-(5-Chloro-7-fluoro-2-(triethylsilyl)-1H-indol-3- yl)ethyl)-4-(3-fluorobenzyl)benzamide. 4-Chloro-2-fluoro-6-iodoaniline (0.100 g; 0.368 mmol), 4-(3-fluorobenzyl)-N-(4- (triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.368 mmol), bis(diphenylphosphino)ferrocene]palladium(ll) chloride (0.015 g; 0.018 mmol), lithium chloride (0.016 mg; 0.368 mmol) and sodium carbonate (0.078 g; 0.737 mmol) were suspended in DMF (5 ml_) and the mixture was stirred at 100C for 18 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60 % ethyl acetate in heptane) to afford 0.102 g (51 %) of the title compound as a yellow oil. ESI/APCI(+): 539(M+H).

The synthetic route of 216393-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D; REMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; ALLASIA, Sara; MARCHAND, Arnaud; KILONDA, Amuri; CHALTIN, Patrick; WO2012/80221; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 63131-30-6, 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 63131-30-6 as follows.

10 ml test tube reaction of adding 0.2mmol2 – (4-methoxyphenylamino) methyl acetate and 0.01mmol trifluoro methane sulfonic acid copper, in order to 3 ml acetonitrile as the reaction solvent, added under stirring 0.1mmol4-iodophenylamino Carbamoyl ethyl acetate, the (green) LED illumination the reaction solution 1h rear, turns on lathe does reaction solvent, after column separation, the obtained product is nuclear magnetism hydrogen spectrum carbon spectrum and mass spectrum is identified as 1-ethyl 4-methyl 2 – (4-iodo benzoyl) – 3 – ((4-methoxylphenyl) amino) succinate

According to the analysis of related databases, 63131-30-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Technical Institute of Physics and Chemistry of the Chinese Academy of Sciences; WU, LIZHU; GAO, XUEWANG; MENG, QINGYUAN; LEI, TAO; ZHONG, JIANJI; XIANG, MING; TONG, ZHENHE; (21 pag.)CN104230734; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 6940-76-7, The chemical industry reduces the impact on the environment during synthesis 6940-76-7, name is 1-Chloro-3-iodopropane, I believe this compound will play a more active role in future production and life.

4-(3-Chloropropyl)-7-fluoro-4H-benzo[1.4]oxazin-3-one A reaction flask was charged with 6,7-difluoro-4H-benzo[1.4]oxazin-3-one (1.5 g, 8.1 mmol), 1-chloro-3-iodopropane (1.44 g, 8.1 mmol), and Cs2CO3 (4.0 g, 12.2 mmol) in MeCN (10 mL) and stirred at rt for 40 h. The reaction mixture was concentrated, water added, and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (1.88 g, 89%). 1H NMR (CDCl3) d 6.99 (dd, J=8.0 Hz, J=5.6 Hz, 1H), 6.79-6.72 (m, 2H), 4.59 (s, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.62 (t, J=6.0 Hz, 2H) 2.18-2.10 (m, 2H); 13C NMR (CDCl3) d 163.9, 159.1 (d, J=244.1 Hz), 146.4 (d, J=11.9 Hz), 124.9 (d, J=3.0 Hz), 115.4 (d, J=9.6 Hz), 109.5 (d, J=22.7 Hz), 105.4 (d, J=26.2 Hz), 67.7, 42.4, 39.2, 30.1.

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

Reference:
Patent; Skjaerbaek, Niels; Koch, Kristian Norup; Mikael Friberg, Bo Lennart; Tolf, Bo-Ragnar; US2005/209226; (2005); 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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 52548-63-7

To a solution of 5-fluoro-2-iodobenzoic acid (17 g) obtained in Step A of Reference Example 1, copper(I) iodide (2.434 g), potassium carbonate (26.5 g) and N,N,N?,N?tetramethylethylene diamine (3.83 mE) in N,N-dimethylformamide (200 mE) was added 1H-1,2,3-triazole (11.11 mE), and the mixture was stirred overnight at 1000 C. The reaction mixture was filtered through Celite, to the filtrate was added 6N aqueous hydrochloric acid solution at 0 C., and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ ethyl acetate) to give the title compound (5.6 g). 1H NMR (300 MHz, DMSO-d6) delta 7.52-7.69 (2H, m), 7.81 (1H, dd, J=8.7, 4.9 Hz), 8.08 (2H, s), 13.35 (1H,brs).

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 52548-63-7.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 19094-56-5, 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. 19094-56-5, name is 2-Chloro-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Iodo-2-chlorobenzoic acid (20.0 g, 0.071 mol) was added to a solution of 2.0 M oxalyl chloride in dichloromethane (39 ml, 0.078 mol), stirred for suspension, and then 8 drops of DMF solution was added dropwise. After the reaction was carried out for 3 hours, the solution was clarified and the reaction was almost complete. The solvent was spin-dried on a rotary evaporator, then 15 ml of methylene chloride was added, and the solvent was dried. After spin-drying, add 30 ml of dichloromethane, stir, cool to 0-5 ° C, add fluorobenzene (7. lg, 0.074 mol), add anhydrous aluminum trichloride (9.9 g, 0.074 mol) in batches, control The temperature is not more than 5 °C, after the completion of the addition, stirring is continued at 4 ° C for 1 h, the reaction is almost complete by TLC, the reaction is quenched on ice-water mixture, the organic phase is separated, and the aqueous phase is extracted with dichloromethane. The phase was washed twice with 1 mol/L hydrochloric acid, washed once with water, and washed twice with 1 mol/L NaOH solution.The mixture was washed twice with saturated sodium chloride and dried over anhydrous sodium sulfate. Drain filtration, spin dry solvent to obtain oilAfter column chromatography, 20. 1g (78.6percent) of a white solid was obtained.

The synthetic route of 2-Chloro-5-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huarun Shuang He Pharmaceutical Co., Ltd.; Zhai Jianguo; He Yang; Zhu Yingjie; Zhou Yisui; Ma Hongmin; Song Meng; (46 pag.)CN108218928; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com