Month: March 2021

Synthetic Route of 162744-59-4, Adding some certain compound to certain chemical reactions, such as: 162744-59-4, name is (4-Bromo-2,6-difluorophenyl)methanol,molecular formula is C7H5BrF2O, 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 162744-59-4.

0.7 g (7.7 mmol 10 eq) of manganese dioxide is added to a solution of 1.0 g (0.77 mmol, 1 eq) of 2,6-difluoro-4-bromobenzylalcool in 15 mL of dichloromethane. The reaction medium is stirred at room temperature for 48 hours.The solid is filtered off and the solvent is evaporated off. The residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate) and 760 mg of 4-bromo-2,6-difluorobenzaldehyde are obtained. Yield = 76%

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; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
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Related Products of 50595-15-8, 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.50595-15-8, name is tert-Butyl 2-hydroxyacetate, molecular formula is C6H12O3, molecular weight is 132.16, as common compound, the synthetic route is as follows.

37.6 mg (0.285 mmol) of hydroxyacetic acid tert-butyl ester were dissolved in 10 ml of DMF, 12.4 mg of sodium hydride (55 percent in mineral oil) were added, and the mixture was stirred at room temperature for 15 min. Then 60 mg (0.237 mmol) of 3-bromo-6-(2-fluoro-phenyl)-pyridazine in 2 ml of DMF were added, and the reaction mixture was stirred at 60 ¡ãC for 5 h and at 120 ¡ãC for 5 h. After evaporation to dryness, the crude product was directly employed in the subsequent step.

Statistics shows that 50595-15-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 2-hydroxyacetate.

Reference:
Patent; sanofi-aventis; EP1939181; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 722-92-9, 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.722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, molecular weight is 259.15, as common compound, the synthetic route is as follows.

Intermediate 22: (R)-tert-Butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0745) (0746) A 2 L reactor, equipped with a thermometer, was charged with (R)-2-(tert-butoxycarbonyl)-5-(methylsulfonyl)isoindoline-1-carboxylic acid (110 g, 307.08 mmol) under nitrogen. EtOAc (1000 mL) was added and the resulting mixture was stirred for 1 min. The vessel was then charged with 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (84 g, 307.08 mmol), the resulting mixture was cooled to +10¡ã C. and then pyridine (27.3 mL, 337.79 mmol) was added. The reaction was cooled to +5¡ã C., and T3P (50percent in EtOAc, 274 mL, 460.62 mmol) was added at 5¡ã C. over 15 min. The temperature rose to 13.3¡ã C. over the addition, and the resulting solution was allowed to reach room temperature over 20 minutes and left stirring overnight at room temperature. The mixture was cooled to +5¡ã C., and an aqueous solution of citric acid (1N) was added, followed by 500 mL of EtOAc. Stirring was continued for 15 min, then stirring was stopped and the layers separated. The organic layer was washed with aqueous citric acid (1000 mL), and then twice with saturated aqueous NaHCO3 (1000 mL), followed by brine (1000 mL). The organic layer was separated and concentrated under reduced pressure (bath temperature 32¡ã C.). The crude material was dissolved in 550 mL of EtOH at rt, and water (440 mL) was slowly added dropwise over 15 min. Seed crystals (20 mg), were added, and the mixture was left overnight at 20¡ã C. The precipitate was isolated by filtration, washed with a 4:1 mixture of H2O/EtOH (220 mL), and dried under high vacuum. The title compound (132 g, quantitative) was used in the next step without further purification. (0747) LC/MS: m/z=581 [M?H]?, 583 [M+H]+. 1H NMR (400 MHz, DMSO-d6, mixture of rotamers, 1.9*:1) delta 1.34*, 1.46 (s, 9H), 3.20, 3.21*(s, 3H), 4.69-4.88 (m, 2H), 5.60*, 5.62 (s, 1H), 7.6-7.76 (m, 5H), 7.86-7.92 (m, 1H), 7.98, 8.01*(s, 1H), 8.68*, 8.69 (s, 1H), 10.76 (s, 1H). (0748) The seed crystals were obtained from (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0.5 g, 0.86 mmol, prepared as described above for the large scale preparation of intermediate 22). This material was dissolved in ethanol (2.5 ml). Water (2 ml) was added until the point the mixture just became turbid. Spontaneous crystalization occurred after about 30 seconds, and (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate was obtained after filtration and drying as a colorless solid (0.38 g, 76percent).

The chemical industry reduces the impact on the environment during synthesis 722-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 14320-38-8, Cyclopent-3-enol, 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, 14320-38-8, blongs to alcohols-buliding-blocks compound. Product Details of 14320-38-8

Step (i): l-[(cyclopent-3-en-l-yloxy)methyl]-4-methoxybenzene To a solution of cyclopent-3-en-l-ol (CAS number 14320-38-8; 15 g, 178 mmol) in dry THF (357 ml) at 0 C under nitrogen was added sodium hydride (60%, 9.27 g, 232 mmol). After fizzing had ceased, to this was then added dropwise l-(chloromethyl)-4- methoxybenzene (CAS number 824-94-2; 31.4 ml, 232 mmol). The reaction was then allowed to warm to room temperature for 17 hours. The reaction mixture was quenched by the addition of methanol and then concentrated in vacuo. The organics were partitioned between ethyl acetate and water. The organics were dried over magnesium sulfate, concentrated in vacuo and purified by column chromatography (silica, 0-50%dichloromethane / petrol) to afford the title compound.1H NMR (400 MHz, OCM-d2) delta ppm 2.33 – 2.47 (m, 2 H), 2.49 – 2.66 (m, 2 H), 3.79 (s, 3 H), 4.20 – 4.32 (m, 1 H), 4.40 (s, 2 H), 5.62 – 5.75 (m, 2 H), 6.86 (d, 7=8.59 Hz, 2 H), 7.24 (d, 7=8.59 Hz, 2 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14320-38-8, its application will become more common.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 111-46-6, 2,2′-Oxybis(ethan-1-ol), 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: 111-46-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 111-46-6

The preparation of this compound was adapted from a literature procedure. Into a suspension of tBuOK (5.10 g, 45.5 mmol) in dry THF (125 mL) was added die(thylene)glycol (9.55 g, 90.0 mmol) at 0 C under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 30 min then propargyl bromide (6.69 g, 45.0 mmol) in dry THF (25 mL) was added dropwise. The resulting mixture was allowed to stir at room temperature for 12 h. After completion of the reaction as indicated by NMR, the mixture was diluted with THF and filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (Si02, EtOAc) to give the product as a pale yellow liquid (4.77 g, 93%). NMR (500 MHz, CDC13) delta 4.22 (d, J = 2.4, 2H, CH2C?C), 3.78 – 3.69 (m, 6Eta, CH2), 3.67 – 3.58 (m, 2Eta, CH2OH), 2.45 (t, J = 2.3, 2H, C?CH, OH). 13C NMR (126 MHz, CDC13) delta 79.6 (CH2C?CH), 74.8 (CH2C?CH), 72.6, 70.4, 69.3, 61.9 (CH2OH), 58.6 (CH2C?CH). The spectroscopic data of 39c are in agreement with those previously reported.

The synthetic route of 111-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PERCEC, Virgil; WO2014/190024; (2014); A1;,
Alcohol – Wikipedia,
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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. 15852-73-0, name is (3-Bromophenyl)methanol, molecular formula is C7H7BrO, 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. Computed Properties of C7H7BrO

Step 1 c’: Synthesis of (4′-(Trifluoromethyl)-[1 ,1 ‘-biphenyl]-3-yl)methanol To a solution of 3-bromo benzyl alcohol (0.1 g, 0.53 mM) and 4- (trifluoromethyl)phenyl)boronic acid (0.121 g, 0.64 mM), DMF/water (8:1 ), Na2C03 (0.142 g, 1 .33 mM) and PdCI2(PPh3)2 (0.010 mM) were added. The reaction mixture was heated in a microwave at 1 10 ¡ãC for 6 min. The reaction mixture was quenched with water and extracted with ethyl acetate (3×10 ml). The organic layer was washed with brine, dried over Na2S04 and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 100-200 mesh, eluted with 15percent ethyl acetate in petroleum ether) to afford the title compound (4’-(trifluoromethyl)-[1 ,1 ‘- biphenyl]-3-yl)methanol as a colorless oil. Yield: 0.108 g( 80percent);1H NMR (DMSO-d6, 300 MHz): delta 7.91 (d, J=8.1 Hz, 2 H), 7.84-7.82 (m, 3 H), 7.70 (m, 1 H), 7.50-7.48 (m, 2H), 5.30 (t, J = 5.7Hz, 1 H, OH), 4.60 (d, J=5.7 Hz, 2 H); MS: m/z 275 (M+Na).

With the rapid development of chemical substances, we look forward to future research findings about 15852-73-0.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; MAHAJAN, Vishal, Ashok; SAWARGAVE, Sangameshwar, Prabhakar; WO2013/128378; (2013); A1;,
Alcohol – Wikipedia,
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Application of 552331-15-4, 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 552331-15-4, name is 1-(5-Bromo-2-fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step-2: Synthesis of 1-(5-bromo-2-fluorophenyl)ethan-1-one To a stirred solution of 1-(5-bromo-2-fluorophenyl)ethan-1-ol (5.3 g, 24.195 mmol, 1.0 eq) in THF (50 mL) was added Dess-martin peridionane (12.314 g, 29.034 mmol, 1.2 eq) at 0 C. The resulting mixture was stirred at rt for 15 min. The progress of reaction was monitored by LCMS. The resection mixture was quenched with saturated solution of NaHCO3 (50 mL) extracted with EtOAc (2*50 mL). The combined organic extracts were washed with water (50 mL), with brine (50 mL) dried over Na2SO4 and concentrated under reduced pressure and purified by flash chromatography [silica gel 100-200 mesh; elution 0-5% EtOAc in hexane] to afford the desired compound 1-(5-bromo-2-fluorophenyl)ethan-1-one (3.78 g, 72.00%) as yellow liquid. 1H NMR (400 MHz, CDCl3) delta 7.99 (dd, J=2.63, 6.58 Hz, 1H), 7.61 (ddd, J=2.63, 4.39, 8.77 Hz, 1H), 7.05 (dd, J=8.77, 10.09 Hz, 1H), 2.64 (d, J=4.82 Hz, 3H).

According to the analysis of related databases, 552331-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35364-79-5, 2-(3,4-Dichlorophenyl)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, 35364-79-5, blongs to alcohols-buliding-blocks compound. Quality Control of 2-(3,4-Dichlorophenyl)ethanol

To a solution of alcohol 35 (0.5 mmol) in CH2Cl2 (10 mL) at 0 Cwas added TEA (0.55 mmol, 1.1 equiv) and methanesulfonyl chloride(0.55 mmol, 1.1 equiv). The mixture was stirred at 0 C for anadditional 2 h, and concentrated to provide crude compound 36. To a solution of 2-(3,4-dichlorophenyl)ethan-1-ol (0.5 mmol) andK2CO3 (1 mmol, 2 equiv) in DMF was added compound 36(0.5 mmol). The reaction mixture was stirred at 60 C overnight,cooled, and partitioned between H2O (50 mL) and EtOAc (30 mL).The aqueous layer was extracted twice using EtOAc (30 mL 2).The combined organic layers were washed using brine, dried overNa2SO4, and concentrated. The crude material was purified by flashchromatography to give compound 5 (28%): 1H NMR (400 MHz,CDCl3): d 7.78 (d, J 8.0 Hz, 2H), 7.60 (d, J 8.0 Hz, 2H), 7.53 (d,J 8.0 Hz, 1H), 7.48 (d, J 3.6 Hz, 2H), 7.38 (d, J 3.6 Hz, 1H), 7.20(d, J 8.4 Hz, 1H), 7.01 (d, J 3.6 Hz, 1H), 4.97 (s, 2H), 3.88 (t,J 5.6 Hz, 2H), 3.04 (t, J 5.6 Hz, 2H); 13C NMR (100 MHz, CDCl3):d 149.6, 145.0, 139.3, 133.6, 132.5, 132.2, 130.8, 130.3, 130.2, 129.0,128.8, 128.3, 118.7, 117.8, 112.7, 70.0, 62.7, 35.3; HRMS (ESI): Exactmass calcd for C20H16Cl3N2OS [MH] 437.0049, found 437.0051;HPLC analysis: retention time 5.7 min, peak area 97.6%, 80:20CH3CN/H2O.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35364-79-5, its application will become more common.

Reference:
Article; Liang, Dongdong; Li, Linhao; Lynch, Caitlin; Mackowiak, Bryan; Hedrich, William D.; Ai, Yong; Yin, Yue; Heyward, Scott; Xia, Menghang; Wang, Hongbing; Xue, Fengtian; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 84 – 99;,
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Adding a certain compound to certain chemical reactions, such as: 4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, 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: 4461-39-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 4461-39-6

General procedure: A suspension oftert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate5(1 eq.), the corresponding amine (2 eq.) and acetic acid (2 – 5 eq.) in DCE (2 ml) was stirred at RT for 30 min.To this suspension was added sodium triacetoxyborohydride (5 eq.).The resulted mixture was stirred at RT for 18 – 72 hrs.The reaction mixture was diluted with 5 ml of saturated sodium carbonate and extracted with DCM (3 x 10 ml).The combined organic layers were dried over sodium sulfate, filtered and concentratedinvacuo.The crude product was purified by Biotage flash chromatography or was used directly in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yan; Sit, Sing-Yuen; Chen, Jie; Swidorski, Jacob J.; Liu, Zheng; Sin, Ny; Venables, Brian L.; Parker, Dawn D.; Nowicka-Sans, Beata; Lin, Zeyu; Li, Zhufang; Terry, Brian J.; Protack, Tricia; Rahematpura, Sandhya; Hanumegowda, Umesh; Jenkins, Susan; Krystal, Mark; Dicker, Ira D.; Meanwell, Nicholas A.; Regueiro-Ren, Alicia; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1550 – 1557;,
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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. 109-83-1, name is 2-(Methylamino)ethanol. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Methylamino)ethanol

A mixture of 4.50 g (19.17 mmol) of product from 1a, 1.69 g (21.10 mmol) of N-methylaminoethanol (BASF), 6.68 ml (47.90 mmol) of triethylamine and 150 ml dichloromethane is stirred overnight at ambient temperature. The reaction mixture is then washed with 0.5 M HCl, saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried on sodium sulphate and evaporated to dryness in vacuo.C12H19NO4S (273.35)[M+H]+=274TLC: silica gel, dichloromethane/ethanol 19:1, Rf value=0.43

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, 109-83-1, 2-(Methylamino)ethanol.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/197664; (2010); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts