Month: September 2021

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

Application of 148836-41-3, These common heterocyclic compound, 148836-41-3, name is 1-Bromo-4-chloro-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.

Synthesis of Intermediate 1-6-1: 165 ml of dioxane solvent was added to a three-necked flask.5 ml of water, followed by 0.1 mol of 3-boronic acid benzofuran,0.1 mol of 1-bromo-3-chloro-2-iodobenzene,0.25 mol of potassium carbonate,0.001 mol of ferrocene palladium dichloride,Stir the mixture to reflux,After 4 hours, the reaction of the raw materials was completed, and the reaction solution was dried under reduced pressure.Intermediate 1-6-1 was obtained by column chromatography(Yield 71%).

The synthetic route of 148836-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Lv Ren Science And Technology Co., Ltd.; Lv Yao; Feng Meijuan; (40 pag.)CN109206431; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 89488-57-3, name is 1,4-Diiodo-2-nitrobenzene, 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 89488-57-3, SDS of cas: 89488-57-3

(RS)-1-(4-Iodo-2-nitrophenyl)-2,2-dimethyl-1-propanol: Under a nitrogen atmosphere a solution of 1,4-diiodo-2-nitrobenzene (3.0 g, 8.0 mmol) in anhydrous THF (20 mL) was cooled to minus 40 C., and then a solution of phenylmagnesium chloride (2 M in THF, 4.8 mL, 9.6 mmol) was added dropwise at a rate that the temperature would not exceed minus 35 C. Upon completion of the addition the mixture was stirred for ten minutes, followed by addition of trimethylacetaldehyde (1.2 mL, 11.2 mmol), and the mixture was stirred for 30 minutes at minus 40 C. The mixture was gradually warmed up to room temperature, quenched with saturated ammonium chloride (60 mL), poured into water (120 mL), and extracted with ethyl acetate twice (60 mL each). The combined organic phase was washed with water (60 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography to yield racemic (RS)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propanol (2.17 g, 81%) as a brown oil. 1H NMR (400 MHz, CDCl3): delta 8.04 (d, 1 H, J=1.6 Hz, Ph-H), 7.88 (dd, 1 H, J=1.6 and 8.4 Hz, Ph-H), 7.51 (d, 1 H, J=8.4 Hz, Ph-H), 5.28 (d, 1 H, J=3.6 Hz, Ph-CH), 2.29 (d, 1 H, J=3.6 Hz, OH), 0.85 (s, 9 H, C(CH3)3). 13C NMR (100 MHz, CDCl3): delta 149.87 (C), 141.0 (CH), 136.2 (C), 132.3 (CH), 131.63 (CH), 91.85 (C), 74.33 (CH), 36.81 (C), 25.6 (CH3).

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; Lasergen, Inc.; Litosh, Vladislav A.; Hersh, Megan N.; Stupi, Brian P.; Wu, Weidong; Metzker, Michael L.; US9200319; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 689260-53-5, These common heterocyclic compound, 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, 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.

Step 1: [(3R,4R)-4-(4-Bromo-3,5-dimethyl-phenoxy)-tetrahydrofuran-3-yloxy]-tert-butyl-dimethyl-silane CuI (0.12 g) and 1,10-phenanthroline (0.23 g) are added to a flask charged with a stir bar, 2-bromo-5-iodo-m-xylene (2.00 g), (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydrofuran-3-ol (1.72 g), Cs2CO3 (4.11 g), and toluene (10 mL) at room temperature. The mixture is stirred at 115 C. overnight. After cooling to room temperature, water is added, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with aqueous 1 M HCl solution and dried (MgSO4). The solvent is evaporated, and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 49:1) to give the title compound. Mass spectrum (ESI): m/z=401/403 (Br) [M+H]+.

The synthetic route of 689260-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; WAGNER, Holger; PETERS, Stefan; (46 pag.)US2018/208560; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 41860-64-4,Some common heterocyclic compound, 41860-64-4, name is 4-Fluoro-2-iodo-1-nitrobenzene, molecular formula is C6H3FINO2, 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.

A. 5-fluoro-4′-methylsulfinyl-2-nitrobiphenyl sulfide p-Methylsulfinylthiophenol 0.2 mole) is dissolved in dry tetrahydrofuran (100 ml.) and sodium hydride (50% dispersion in mineral oil, 0.2 mole) is added over 30 minutes. The solution is evaporated to dryness and the residue rinsed well with n-hexane. The powdered salt is stirred under N2 at reflux with 4-fluoro-2-iodonitrobenzene (0.2 mole) in dry dimethylformamide for 16 hours, evaporated to dryness and extracted into chloroform (3 * 200 ml.). The organics are washed with water (2 * 100 ml.), separated and dried (MgSO4). The solution is filtered, evaporated to dryness and put on a column of silica-gel (Baker 2 in. * 2 ft.) and various fractions eluted with portions of benzene-n-hexane. In this way, pure 5-fluoro-4′-methylsulfinyl-2-nitrobiphenyl sulfide is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-2-iodo-1-nitrobenzene, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US3954852; (1976); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 627-31-6, These common heterocyclic compound, 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), 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.

Diiodopropane (0.52 mL, 4.50 mmol, 5 eq) and potassium carbonate (124 mg, 0.90 mmol, 1 eq) were added to a solution of phenol 40 (500 mg, 0.90 mmol) in acetone (5 mL, dried over molecular sieves). The reaction mixture was then warmed to 60C and stirred for 3 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 42 (450 mg, 70% with some impurities due to elimination reaction). LC/MS, method 2, 3.90 min (ES+) m/z (relative intensity) 722.33 ([M+H]+, 100).

Statistics shows that 1,3-Diiodopropane(stabilized with Copper chip) is playing an increasingly important role. we look forward to future research findings about 627-31-6.

Reference:
Patent; SPIROGEN SARL; HOWARD, Philip Wilson; TIBERGHIEN, Arnaud; WO2013/53872; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, molecular formula is C7H6BrIO, 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. Safety of 1-Bromo-4-iodo-2-methoxybenzene

Step 1: 3-(4-bromo-3-methoxyphenyl)thiophene-2-carboxylic acid A solution of 3-(dihydroxyboryl)thiophene-2-carboxylic acid (1.89 g, 10.85 mmol) and 1-bromo-4-iodo-2-methoxybenzene (3.09 g, 9.86 mmol) in a 3:1 mixture of MeCN:H2O (100 mL) was treated with K2CO3 (4.09 g, 29.6). Pd(OAc)2 (66.4 mg, 0.30 mmol) and biphenyl-2-yl(dicyclohexyl)phosphine (207 mg, 0.59 mmol) were added and the mixture was stirred at 90 C. for 3 h. The mixture was cooled and concentrated, and the residue was added at 0 C. to a mixture of 10% aqueous NaOH (100 mL) and DCM. The mixture was acidified to pH=1 by addition of aqueous HCl (6 N) and the solid precipitate was collected by filtration, washed with cold H2O and DCM, then dried to afford the title compound (2.29 g, 74%). LCMS (ES) m/z 313, 315 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 755027-18-0, its application will become more common.

Reference:
Patent; Harper, Steven; Summa, Vincenzo; Liverton, Nigel J.; McCauley, John A.; Butcher, John W.; Di Filippo, Marcello; Di Francesco, Maria Emilia; Ferrara, Marco; Romano, Joseph J.; Rudd, Michael T.; US2010/183551; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 33348-34-4, 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 33348-34-4 as follows.

A solution of the product of Step A (0.32 g, 1 .31 mmol) and 1 M NaN(SiMe3)2 in THF (2.62 ml) in anhydrous THF (2 ml) was stirred at ~-5C for 30 min under N2. To it acetyl chloride (0.1 1 ml, 1 .44 mmol) was and the mixture was stirred overnight at room temperature, than evaporated to dryness under reduced pressure. The residue was diluted to 50 ml with EtOAc, washed with H20, brine, dried over anhydrous MgS04, filtered and the filtrate evaporated to dryness. The residue was purified by crystallization from MeOH to give the title compound (0.26 g, 70%), as colourless solid. 1 H NMR (CDCI3) 8.46 (d, 1 H, J = 9 Hz), 8.03 (s, 1 H), 7.58 – 7.63 (m, 2H), 2.27 (s, 3H).

According to the analysis of related databases, 33348-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AKAAL PHARMA PTY LTD; GROBELNY, Damian W; GILL, Gurmit S; WO2014/63199; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 391211-97-5, 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 391211-97-5 as follows.

A dry 100 mL round bottomed flask was charged with a mixture of the substituted benzoic acid, and 5 mL of DCM. The reaction mixture was cooled with an ice-bath to 0 oC. A 100 muL volume of anhydrous DMF was added followed by dropwise addition of neat oxalyl chloride (2 equiv.) over 5 min. The reaction was stirred at 23 oC for 4 h. The solvent was removed under reduced pressure. Excess oxalyl chloride was azeotropically removed with 2 X 5 mL portions of DCM under reduced pressure. The crude acid chloride was dissolved into 5 mL of DCM and a greater than 2-fold stoichiometric ratio the appropriate amine was added neat at 0 oC. The ice bath was removed after 10 min and the reaction was permitted to warm to room temperature. The reaction was then stirred at 23 oC for 6 h; completion of reaction was determined by TLC. A mixture of 10 mL of H2O and 10 mL of Et2O was added and the resultant mixture was extracted with twice with 10 mL portions of Et2O, washed twice with 10 mL portions of NaCl (aq, sat), and dried over Na2SO4. The extract was decanted and then the solvent was removed under reduced pressure. The crude product was isolated on SiO2 using hexane/EA.

According to the analysis of related databases, 391211-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chakrabarty, Suravi; Monlish, Darlene A.; Gupta, Mohit; Wright, Thomas D.; Hoang, Van T.; Fedak, Mitchel; Chopra, Ishveen; Flaherty, Patrick T.; Madura, Jeffry; Mannepelli, Shankar; Burow, Matthew E.; Cavanaugh, Jane E.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 13; (2018); p. 2294 – 2301;,
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 101335-11-9 as follows. Formula: C6H3ClFI

Step 1. Ethyl 2-(4-(2-chloro-4-fluorophenyl)-4-hydroxycyclohexyl)acetate. A solution of n-butyllithium in hexanes (1.6 M, 81.4 mL, 130 mmol) was added dropwise to a solution of 2- chloro-4-fluoro-l-iodobenzene (16.6 mL, 130 mmol) in tetrahydrofuran (197 mL) at -78C. The reaction mixture was allowed to stir at -78C for 1 h before the addition of ethyl 2-(4- oxocyclohexyl)acetate (19.2 mL, 109 mmol) in one portion. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction was quenched with a saturated solution of ammonium chloride (500 mL) and extracted with EtOAc (3 x 150 mL), combined organics dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica, eluting with 0-40% EtOAc in hexanes to yield the product as a colorless oil (26.7 g, 78%). 1H NMR (400 MHz, CDCb) d 7.65 (dd, / = 8.86, 6.30 Hz, 1H), 7.21 – 7.09 (m, 1H), 7.03 – 6.94 (m, 1H), 4.27 – 4.07 (m, 5H), 2.62 – 2.47 (m, 2H), 2.46 – 2.18 (m, 10H), 2.15 – 1.82 (m, 6H), 1.78 – 1.34 (m, 7H), 1.34 – 1.22 (m, 7H). [M-H2O+H] = 283.1.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com