Month: June 2021

Electric Literature of 748805-85-8, 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 748805-85-8 as follows.

General procedure: A solution of 4-toluene sulfonyl chloride (4.58 g, 1.2 equiv) or methanesulfonyl chloride (1.9 mL, 1.2 equiv) and pyridine (2 mL, 1.3 equiv) in 20 mL CH2Cl2 was added slowly to the solution of compound 11 (0.02 mol) in 40 mL CH2Cl2. The mixture was stirred overnight at room temperature. Then 30 mL diluted HCl solution was added to the reaction mixture, the organic layer was separated using separating funnel. Subequently, the aqueous phase was extracted with 15 mL CH2Cl2 three times, the combined organic layers were washed separately with saturated NaHCO3 (30 mL) and saturated NaCl (30 mL) three times. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography using petroleum ether/EtOAc = 1/1 to give the product 12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,748805-85-8, its application will become more common.

Reference:
Article; Xu, Changrui; Wu, Zhengxing; Chen, Jianzhong; Xie, Fang; Zhang, Wanbin; Tetrahedron; vol. 73; 14; (2017); p. 1904 – 1910;,
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Electric Literature of 1261524-75-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1261524-75-7, name is 3-Bromo-2-chlorobenzyl Alcohol, molecular formula is C7H6BrClO, molecular weight is 221.48, as common compound, the synthetic route is as follows.

To a solution of (3-bromo-2-chlorophenyl)methanol(4.57 g, 20.63 mmol, 1 equiv.) in DCM(200 mL) were added DMF(45.2 mg, 0.62 mmol, 0.03 equiv.) and SOCl2(61.4 g, 516.10 mmol, 25.01 equiv.) dropwise at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 2 days at ambient temperature. The desired product could be detected by LCMS. The mixture was concentrated to get crude product. The crude product was added water(400mL) and extracted with EA (400mLx2). The organic layers was washed with saturated brine (200ml), dried over anhydrous Na2SO4, filtered and concentrated to give desired product. The residue was purified by silica gel column chromatography, eluted with EtOAc / PE (1:50 to 1:40) to afford 1-bromo-2-chloro-3-(chloromethyl)benzene (4.9 g, 98.98%) as a yellow liquid.

The chemical industry reduces the impact on the environment during synthesis 1261524-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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Application of 2612-28-4, 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. 2612-28-4, name is 2-Propylpropane-1,3-diol, molecular formula is C6H14O2, The 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.

EXAMPLE 5 A mixture of 1.2 g of 2-propylpropane-1,3-diol, 2.59 g of 5-(2-pentyl-5-pyridyl)-2-formyl-thiophene (obtainable by formylation of 5-(2-pentyl-5-pyridyl)-thiophene via a Vilsmeier reaction), 0.01 g of p-toluenesulfonic acid and 15 ml of toluene is boiled for 3 hours, using a water separator, cooled, washed with water and evaporated. 5-(2-Pentyl-5-pyridyl)-2-(trans-5-propyl-1,3-dioxan-2-yl)-thiophene is obtained.

According to the analysis of related databases, 2612-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent Gesellschaft Mit Beschrankter Huftung; US4659503; (1987); A;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.7589-27-7, name is 2-(4-Fluorophenyl)ethanol, molecular formula is C8H9FO, molecular weight is 140.16, as common compound, the synthetic route is as follows.Recommanded Product: 7589-27-7

To a 50 mL round bottom flask equipped with a stir bar was added 6-chloropyridazin-3-ol (250 mg, 1.9 15 mmol), 2-(4-fluorophenyl)ethanol (268 mg, 1.9 15 mmol), triphenylphosphine (603 mg, 2.298 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.447 mL, 2.298 mmol). The solution had a mild exotherm, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reaction solution was concentrated in vacuo and purified via silica gel chromatography (40 gcolumn, 5-40percent EtOAc:Hex) to afford the semi pure product. The material was further purfied via reverse phase C18 chromatography (55 g column, 20-100percent CH3CN:Water with 0.1percent TFA buffer). The desired fractions were isolated, diluted with sat. sodium bicarbonate solution (25 mL) and EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, and volatiles evaporated to afford the pure product 3-chloro-6-(4-fluorophenethoxy)pyridazine (450 mg, 1.781 mmol, 93 percent yield) as a white solid. 1H NMR (400 MHz, CDC13) 7.22 (dd, J=8.3, 5.4 Hz, 2H), 7.18 (d, J=9.8 Hz, 1H), 7.04 – 6.97 (m, 2H), 6.91 (d, J9.5 Hz, 1H), 4.37 -4.30 (m, 2H), 3.13 – 3.06 (m, 2H). LCMS (M+1) = 253.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7589-27-7, 2-(4-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Synthetic Route of 495-76-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol, molecular formula is C8H8O3, molecular weight is 152.1473, as common compound, the synthetic route is as follows.

To a solution of the piperonyl alcohol (8) (2.0 g, 13.15 mmol) in anhydrous CH2Cl2 (30 mL), cooled to 0 C and stirred, under an argon atmosphere, freshly distilled PBr3 (3.7 mL, 39.45 mmol), was added dropwise. The resulting solution was kept under stirring at 0 C for a further 20 minutes. After, the ice bath was removed, maintaining the stirring for a further 2 h. The system was cooled again to 0 C and a saturated solution of NaHCO3 (75 mL) was slowly added. Extraction was carried out with ethyl ether (3x 70 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford crude bromide (9). This bromide (used immediately after its preparation) was solubilized with anhydrous acetonitrile (30 mL), treated with triphenylphosphine (3.45 g, 13.15 mmol) and stirred overnight, under reflux. Acetonitrile was removed under reduced pressure and the residue was recrystallized from ethanol to provide (5.21 g) Wittig salt (10) in 83% overall yield. Rf 0.53 (CH2Cl2/MeOH 9:1). mp: 237.2-238.5 C. IR (neat) numax/cm-1: 3018, 1492, 1438, 1246, 1109, 750, 687. 1H NMR (400 MHz, CDCl3) delta 7.80-7.62 (m, 15H), 6.62-6.59 (m, 1H), 6.53 (d, 2H, J=5.5 Hz), 5.87 (s, 2H), 5.28 (d, 2H, J=13.9 Hz). 13C NMR (100 MHz, CDCl3) delta 147.6, 134.9 (d, J=11.5 Hz), 134.2 (d, J=38.6 Hz), 130.0 (d, J=49.7 Hz), 125.3, 119.9 (d, J=36 Hz), 118.0, 117.2, 111.2 (d, J=18.4 Hz), 108.4 (d, J=13.5 Hz), 101.1, 30.4 (d, J=187.4 Hz). HRMS (ESI+) calcd for C26H22BrO2P [M-HBr]+ 397.1352, found 397.1358.

Statistics shows that 495-76-1 is playing an increasingly important role. we look forward to future research findings about Benzo[d][1,3]dioxol-5-ylmethanol.

Reference:
Article; Diaz-Munoz, Gaspar; Isidorio, Raquel Geralda; Miranda, Izabel Luzia; de Souza Dias, Gabriel Nunes; Diaz, Marisa Alves Nogueira; Tetrahedron Letters; vol. 58; 33; (2017); p. 3311 – 3315;,
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Application of 87327-65-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 87327-65-9, name is 1-(2,6-Difluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Example 82; 5- [1-(2,6- Difluorophenyl)-ethoxy ]-q uinazoline-2,4-diamine; [00258] Step 1; To a cold (ice water) suspension of sodium hydride (409 mg; 10 mmol) in anhydrous DMF (4 mL) is added a solution of 2,6-difluoro-alpha- methylbenzyl alcohol (1.63 g; 10 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 1 hour, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1.53 g; 11 mmol) in anhydrous DMF (6 mL), and allowed to room temperature over 2.5 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting solid is filtered, washed with water, and dried under vacuum at 40 C overnight to give 1.92 grams of 2-[ 1-(2,6-difluorophenyl)-ethoxy]-6-fluorobenzonitrile.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 87327-65-9, 1-(2,6-Difluorophenyl)ethanol.

Reference:
Patent; DECODE CHEMISTRY, INC.; SINGH, Jasbir; GURNEY, Mark E.; WO2005/123724; (2005); A1;,
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Electric Literature of 162744-59-4 ,Some common heterocyclic compound, 162744-59-4, molecular formula is C7H5BrF2O, 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.

Example A-14; 2-(4-bromo-2,6-difluorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-5-carboxamide; Step a – 4-bromo-2,6-difluorobenzaldehyde; To a solution of 4-bromo-2,6-difluorobenzylalcohol (0.20Og, 0.9mmol) in DCM (4ml) and DMSO (0.440ml) was added triethylamine (1 ml, 0.72mmol) and sulfur trioxide pyridine complex (0.57Og, 3.6mmol) and the resulting solution was stirred at room temperature for 3 hours. The solution was diluted with Et2O and washed with 0.5M aqueous HCI, 1M sodium bicarbonate solution and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 4-bromo-2,6-difluorobenzaldehyde (0.166g, 0.75mmol, 84%) as a white solid. 1H NMR (CDCI3) delta 7.22 (2H, d), 10.29 (1 H, br. s). LCMS (2) Rt: 2.74min.

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. 162744-59-4, (4-Bromo-2,6-difluorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAREUM LIMITED; WO2008/139161; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 552331-15-4, 1-(5-Bromo-2-fluorophenyl)ethanol, 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, Recommanded Product: 1-(5-Bromo-2-fluorophenyl)ethanol, blongs to alcohols-buliding-blocks compound. Recommanded Product: 1-(5-Bromo-2-fluorophenyl)ethanol

Step 2 [0202] To a solution of Compound 2 (14.01 g) in ethyl acetate (150 ml) was added 2-iodoxybenzoic acid (35.8 g), and the mixture was refluxed for 7 hours. The reaction solution was cooled in an ice bath and the precipitated solid was removed by filtration. The filtrate was evaporated under reduced pressure to afford Compound 3 (13.66 g) [0203] 1H-NMR (CDCl3) delta: 2.64 (d, J=5.0 Hz, 3H), 7.05 (dd, J=10.2, 8.7 Hz, 1H), 7.58-7.64 (m, 1H), 7.98 (dd, J=6.4, 2.5 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,552331-15-4, 1-(5-Bromo-2-fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; SHIONOGI & CO., LTD.; Masui, Moriyasu; Tadano, Genta; US2013/210839; (2013); A1;,
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Application of 2002-24-6, Adding some certain compound to certain chemical reactions, such as: 2002-24-6, name is 2-Aminoethanol hydrochloride,molecular formula is C2H8ClNO, 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 2002-24-6.

Step A N-tritylethanolamine Ethanolamine hydrochloride (9.9 g; 100 mmol) is partially dissolved in CH2 Cl2 /CH3 CN (200 ml/100 ml) and Et3 N (23 ml; 170 mmol) is then added. Tritylchloride (18.9 g; 67.6 mmol) is added portionwise over 30 minutes. After the addition is complete the reaction mixture is allowed to stir an additional 30 minutes, diluted with CH2 Cl2, washed With H2 O 2* and brine, dried (MgSO4), concentrated in vacuo and purified by column chromatography with silica/CH2 Cl2 to give N-tritylethanolamine as an oil which is used directly in Step B.

According to the analysis of related databases, 2002-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rhone-Poulenc Rorer Pharmaceuticals Inc.; US5455260; (1995); A;,
Alcohol – Wikipedia,
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Application of 140373-17-7 , The common heterocyclic compound, 140373-17-7, name is 2-Amino-2-(4-fluorophenyl)ethanol, molecular formula is C8H10FNO, 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.

Method E, Step 5Compound E5 will be reacted with E6 and EDCI in DMF to give compound E7 after purification.

The synthetic route of 140373-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/61699; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts