Category: 14452-30-3

Application of 14452-30-3,Some common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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: Arylhalide (1a,b18a,b, 1.2 equiv, typically ca. 50 mg), NNCu(bdmpphen) (1.0 equiv, typically ca. 50 mg), Pd2(dba)3¢CHCl3 (5 mol% in most cases), and DPPF (10 mol% in mostcases) were dissolved in dry THF under nitrogen. The mixturewas refluxed until the starting Cu-complex was consumed(monitored by TLC, typically 30min in most cases for ArI).After the reaction mixture was concentrated under reducedpressure, toluene (3 mL) was added into the residue. The residualmixture was separated and purified by chromatography,to afford the corresponding cross-coupling product.

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

Reference:
Article; Yamada, Kiyomi; Zhang, Xun; Tanimoto, Ryu; Suzuki, Shuichi; Kozaki, Masatoshi; Tanaka, Rika; Okada, Keiji; Bulletin of the Chemical Society of Japan; vol. 91; 7; (2018); p. 1150 – 1157;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 14452-30-3, A common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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: A mixture of Cu2O (Sigma-Aldrich, 99.99% purity, 0.147 mmol), Cs2CO3 (2.94 mmol),distilled water (0.2 mL), aryl halide (1.47 mmol) and p-toluenesulfonic acid (TsOH) solution(0.3 mL, 2.45 mol/dm3) were added to a reaction vial and a screw cap was fitted to it. Thereaction mixture was stirred under air in a closed system at 120 C for 24 h, following whichthe heterogeneous mixture was cooled to room temperature and diluted with dichloromethane.The combined organic extracts were dried with anhydrous Na2SO4 and the solvent wasremoved under reduced pressure. The crude product loaded into the column using minimalamounts of dichloromethane and was purified by silica-gel column chromatography to affordthe N-arylated product. The identity and purity of products was confirmed by 1H and 13CNMR spectroscopic analysis.

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tan, Bryan Yong-Hao; Teo, Yong-Chua; Synlett; vol. 27; 12; (2016); p. 1814 – 1819;,
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 14452-30-3 as follows. name: 1-(3-Iodophenyl)ethanone

Ethyl 3-(3-iodophenyl)-3-oxopropanoate (0481) To a solution of diethyl carbonate (12.0 g, 101.6 mmol) in anhydrous toluene (100 mL) was added NaH (60% suspension in mineral oil, 3.25 g, 81.3 mmol) portionwise at 0 C under nitrogen atmosphere. After stirring at 0 C for 5 minutes, the mixture was warmed up to room temperature and l-(3-iodophenyl)ethanone (5.0 g, 20.3 mmol) was added dropwise over 10 minutes. The resulting mixture was heated at 110 C for 16 hours. The reaction was cooled to 0 C and quenched with CH3COOH (10 mL). H20 (50 mL) was added and the mixture was extracted with EtOAc (100 mL x 2). The combined organic layers were washed with saturated aqueous NaHC03 (100 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silical gel (0- 5 % EtOAc/PE) to afford the desired product as a red oil (4.0 g, 62% yield). 1H NMR (400 MHz, CDC13) delta 8.28 (s, 1H), 7.92 (d, / = 8.8 Hz, 1H), 7.90 (d, / = 8.0 Hz, 1H), 7.25-7.21 (m, 1H), 4.22 (q, / = 7.2 Hz, 2H), 3.95 (s, 1H), 1.27 (t, / = 7.2 Hz, 3H). LCMS (ESI): m/z 318.8 [M+H]+, RT = 0.93 min (LCMS Method E).

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; GEHLING, Victor S.; HARMANGE, Jean-Christophe; LAI, Tommy; LIANG, Jun; DRAGOVICH, Peter; ORTWINE, Dan; LABADIE, Sharada; ZHANG, Birong; KIEFER, Jim; WO2015/135094; (2015); 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. 14452-30-3, name is 1-(3-Iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(3-Iodophenyl)ethanone

Step A: 4-(3-Iodo-phenyl)-2,4-dioxo-butyric acid methyl ester Sodium hydride (60% oil dispersion, 4.9 g, 123 mmol) was added in portions to a solution of 3-iodoacetophenone (25.18 g, 102.3 mmol) and dimethyl oxalate (14.5 g, 123 mmol) in DMF (125 mL) at 0 C. The mixture stirred at room temperature for 1 hour and was then heated at 115 C. for 1 h. After cooling, the mixture was treated with 3 M HCl and then diluted with ethyl acetate. The organic layer washed three times with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. Chromatography on silica gel, 0-10% ethyl acetate in hexanes, afforded 24.2 g of the subtitle compound (71.3% yield) as a yellow solid which was used directly in the next step.

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS, INC.; US2007/259895; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 14452-30-3,Some common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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.

To a cooled (-40 C) stirred solution of TiC4 (11 mL of a 1. OM sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5. 5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min iodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an additional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnisium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil.

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (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. 14452-30-3, name is 1-(3-Iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 14452-30-3

General procedure: All the chemicals and solvents were purchased from Sigma Aldrich. The progress of all reactions was monitored on Merck KGaA precoated silica gel plates 0.25 mm (with fluorescence indicator UV254) using ethyl acetate/n-hexane as solvent system. Spots were visualized by irradiation with ultraviolet light (254 nm). Melting points (mp) were determined using open capillary method on Melting Point III Marte apparatus. Proton (1H) and (13C) NMR spectra were recorded on Bruker Avance 400 spectrometer at 400 MHz for 1H and 100 MHz for 13C using DMSO-d6 and CDCl3 as solvents referenced. Chemical shifts are given in parts per million (ppm) (delta relative to residual solvent peak for 1H and 13C). Spectra Mass was performed on a LCMS-2020 Liquid Chromatograph Mass Spectrometer Shimadzu, the column was Agilent XDB-C18, 35 muM, 21×20 nm. IR spectra were recorded on a PerkinElmer model Spectrum 400 (medium, sweep of 4000 to 400 cm-1). Synthesized compounds were ?96% pure as determined by high performance liquid chromatography (HPLC) Shimadzu with PDA detector, Nucleodur 100-5 CN-RP column 205×4.6mm, mobile phase water/0.1% TFA and acetonitrile with flow of 1mL/min. For the synthesis of 3-25, substituted acetophenones (0.5 equiv, 0.5 mmol) and nitroaromatics (0.5 equiv. 0.5 mmol) were dissolved in acetic acid (1mL) and concentrated sulfuric acid (0.05 mL) and were stirred at 100C until completion of the reaction (4-24h). The cooled mixture and the solid was washed with iced methanol (200 mL) for purification. For the synthesis of 26-35, 0.4 mL of aqueous NaOH (20% w/v) was added to the solution of the acetophenones substituted in 4? position (1 mmol) in EtOH. The resulting mixture was stirred at the room temperature for 10 h. The formed precipitate was filtered and washed with cold water. If no precipitation occurred, the resulting mixture was neutralized with 5% HCl filtered and dried. The crude was then subjected to chromatography column with EtOAc/Hexane (7:3, v/v) as eluent.

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gomes, Marcelo N.; Braga, Rodolpho C.; Grzelak, Edyta M.; Neves, Bruno J.; Muratov, Eugene; Ma, Rui; Klein, Larry L.; Cho, Sanghyun; Oliveira, Guilherme R.; Franzblau, Scott G.; Andrade, Carolina Horta; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 126 – 138;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 14452-30-3,Some common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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.

Step 1: 2-(3-iodophenyl)propan-2-ol; To a solution of 3-iodo-acetophenone (15g, 61 mmol) in 10OmL THF at -78 0C was slowly added MeMgBr (6OmL of a 1.4M solution in THF, 84 mmol) and the solution was stirred for 1 hour as it warmed to 0 0C. The reaction was quenched with saturated NH4Cl and the crude product was extracted with ether (2x) and the organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by flash (5-10% EA/hex) to give the desired product.

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/14454; (2007); A1;,
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 14452-30-3 as follows. Computed Properties of C8H7IO

General procedure: The suspension of benzothiazole (1, 250 mumol), aryl halide (2 or 3, 375 mumol), LiOt-Bu (30.0 mg, 375mumol), and 5% Cu/CR (31.8 mg, 25.0 mumol; 5% Cu/CR11 for 2, 5% Cu/CR20 for 3) in 50% i-PrOH (1mL) was stirred at 90 C under argon atmosphere. After 24 h, the mixture was cooled to roomtemperature and filtered through a celite pad. The catalyst on the celite pad was washed with EtOAc (20mL). The combined filtrates were washed with H2O (20 mL) and the aqueous layer was further extractedwith EtOAc (20 mL). The combined organic layers were washed with H2O (20 mL × 3), dried overNa2SO4 and concentrated under decreased pressure. The residue was purified by silica-gel columnchromatography using toluene/EtOAc as an eluent to give a spectrally pure S-aryl-2-thioaniline (4).2-(3′-Acetylphenylthio)aniline (4ab): Obtained in 74% yield (44.9 mg, 184 mumol) from 1a (27.3 muL,250 mumol) and 3′-iodoacetophenone (2b, 92.3 mg, 375 mumol). Slightly brown oil. 1H NMR (500 MHz) delta7.67 (1H, dd, J = 8.0, 1.5 Hz), 7.45 (1H, dd, J = 7.5, 1.5 Hz), 7.29 (1H, dd, J = 8.0, 1.5 Hz), 7.26 (1H, ddd,J = 7.5, 7.5, 1.5 Hz), 7.20 (1H, dd, J = 8.0, 1.5 Hz), 6.80 (1H, dd, J = 7.5, 1.5 Hz), 6.77 (1H, ddd, J = 7.5,7.5, 1.5 Hz), 4.32 (2H, brs), 2.52 (3H, s); 13C NMR (125 MHz) delta 197.6, 148.9, 148.1, 137.7, 137.5, 131.6,130.5, 129.2, 126.1, 125.2, 118.9, 115.4, 113.3, 26.6; HRMS (LCMS-IT-TOF) calcd. for C14H14NOS[(M+H)+] 244.0791, found: 244.0804.

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ichikawa, Tomohiro; Matsuo, Tomohiro; Tachikawa, Takumu; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Heterocycles; vol. 97; 2; (2018); p. 793 – 805;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 14452-30-3, 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 14452-30-3 as follows.

General procedure: Single-pass manner (conditions A and B): A solution of iodoarene (1mmol), alkene (2mmol), and Bu3N (condition A, 1.5mmol; condition B, 3mmol) in DMA (condition A, 10mL; condition B, 4mL) was prepared in a vial and flowed into cartridge A packed with 7% Pd/WA30 at the flow rate of 0.15mLmin-1 along with the MW irradiation (10W) under the 1MPa back-pressure in a single-pass manner. After the entire solution in the vial had passed through the catalyst cartridge, additional DMA (15mL) was passed through the path to wash out the remaining reagents (total operation time: ca. 140 min). To the collected mixture were added EtOAc (20mL) and H2O (10mL), and the layers were separated. The aqueous layer was extracted with EtOAc (20mL). The combined organic layers were washed with H2O (20mL×4) and brine (20mL), dried over Na2SO4, and concentrated in vacuo. To the residue was added CDCl3 (ca. 1.5mL) and 1,4-dioxane (8.53muL, 100mumol) as an internal standard, and the yield was determined by 1H NMR. The 1H NMR sample was diluted with EtOAc (15mL), washed three times with sat. aq. CuSO4 (5mL) and H2O (10mL), dried over Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography using hexane/EtOAc (10: 1) as the eluent to give the corresponding substituted alkenes as the Mizoroki-Heck reaction product. (0023) Circulation manner (condition C): When the TLC analysis revealed that the aryl iodide still remained unreacted after a single-pass of the reaction solution through the catalyst cartridge, both the starting and ending parts of the flow path were dipped into the reaction solution in a reservoir for circulation. After 7.5h of circulation at the flow rate of 0.15mLmin-1, the flow path was washed with DMA (15mL). The recovered mixture was treated according to a procedure similar to that described for the single-pass setup.

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ichikawa, Tomohiro; Mizuno, Masahiro; Ueda, Shun; Ohneda, Noriyuki; Odajima, Hiromichi; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 74; 15; (2018); p. 1810 – 1816;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

14452-30-3, name is 1-(3-Iodophenyl)ethanone, 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. Formula: C8H7IO

General procedure: Aryl halide (1.1 eq.), Au complex 1 (1.0 eq.) and a palladium catalyst (10 mol%) was dissolved in THF under nitrogen. The mixture was refluxed until the starting Au-complex was consumed (monitored by TLC). The reaction mixture was concentrated under reduced pressure. The residue was separated and purified by chromatography, to afford the corresponding cross-coupling product.

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanimoto, Ryu; Suzuki, Shuichi; Kozaki, Masatoshi; Okada, Keiji; Chemistry Letters; vol. 43; 5; (2014); p. 678 – 680;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com