Tag: M.W=200-300

Application of 17100-58-2, Adding some certain compound to certain chemical reactions, such as: 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol,molecular formula is C8H9BrO, 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 17100-58-2.

Intermediate 168: [2′,3-dimethyl-4′-(trifluoromethyl)-4-biphenylyl]methanol; To a solution of (4-bromophenyl)-methanol (Intermediate 15, 2.0 g, 9.8 mmol) and the commercially available [2-methyl-4-(trifluoromethyl)phenyl]boronic acid (2 g, 9.8 mmol) in DME was added a 1 M solution of sodium carbonate (20 ml_, 2 equiv.) then Pd(PPh3)4 (120 mg, 0.01 equiv.) was added and the reaction mixture was heated at 800C for 18 hours. The reaction was filtered on Celite and washed with Et2O. The filtrate was then washed with water and a NaHCO3 solution, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluted with DCM and DCM/MeOH 95/5 to give the title compound. (2.3 g, yield: 84%). 1H NMR: (CDCI3) delta 7.60-7.4 (m, 3H), 7.35 (d, 1 H), 7.2-7.1 (m, 2H), 4.75 (s, 1 H), 2.45 (s, 3H), 2.35 (s, 3H).

According to the analysis of related databases, 17100-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; BOUILLOT, Anne Marie Jeanne; DODIC, Nerina; GELLIBERT, Francoise Jeanne; MIRGUET, Olivier; WO2010/15652; (2010); A2;,
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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.38493-59-3, name is (3-Bromo-4-methoxyphenyl)methanol, molecular formula is C8H9BrO2, molecular weight is 217.06, as common compound, the synthetic route is as follows.name: (3-Bromo-4-methoxyphenyl)methanol

On the basis of Example 1, the other steps were not changed, and the method of step (2) in Example 1 was changed to 10 gCompound B,3-bromo-4-methoxybenzyl alcohol,Adding 8.6 g of m-chlorobenzeneboronic acid,18.8 g of potassium carbonate,Urea 82.8 mg,Palladium acetate 210 mg,Isopropyl alcohol / water solvent 100mL,Stir at room temperature. Until the solid completely dissolved, remove the reaction system of oxygen, anaerobic reaction, heating,After completion of the reaction, the isopropanol and part of the water were removed under reduced pressure, and then extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and the palladium salt was removed by suction filtration. , 11.46 g, yield> 95%. The overall yield of this example was 65.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38493-59-3, (3-Bromo-4-methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Xu Jiangping; Chen Yunfeng; Zhou Zhongzhen; (8 pag.)CN106632070; (2017); A;,
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Synthetic Route of 162744-59-4, 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. 162744-59-4, name is (4-Bromo-2,6-difluorophenyl)methanol, molecular formula is C7H5BrF2O, 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.

Step 1: The preparation of 2,6-difluoro-4-bromobenzyl methanesulphonate; 2,6-difluoro-4-bromobenzyl alcohol (9.50 g) and triethylamine (5.0 g) were dissolved in THF cooled to 10C with stirring. Methanesulphonyl chloride (4.8 g) was added in a solution of THF (10ml) over 10 minutes, and a white solid precipitated from the solution. The reaction was then warmed to room temperature for one hour and then the solid was collected and washed with diethyl ether. The filtrate was evaporated to give 2,6-difluoro-4- bromobenzyl methanesulphonate (13.0 g) as a golden oil which slowly crystallised. ¹H NMR (CDCl3) No. ppm: 3.05 (s, 3H), 5.3 (s, 2H), 7.15 (t,2H).

According to the analysis of related databases, 162744-59-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/123698; (2005); A1;,
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Application of 34598-50-0, 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.34598-50-0, name is 5-Bromo-2,3-dihydro-1H-inden-1-ol, molecular formula is C9H9BrO, molecular weight is 213.07, as common compound, the synthetic route is as follows.

Commercially available 5-bromoindanone (5.1 g, 24.3 mmol) was diluted into methanol (150 mL), cooled to 0 0C, and treated with sodium borohyd?de (1.8 g, 48.6 mmol). The reaction mixture was warmed to room temperature, aged overnight, and then partitioned between water and methylene chloride, the organic phase separated, dried and concentrated in vacuo. The clean crude alcohol (5.0 g, 97%) was isolated and used in the next step without purification. This hydroxybromoindane (5.04 g, 23.6 mmol) was diluted into toluene (100 mL), treated with catalytic p-toluenesulfomc acid (400 mg), and the reaction mixture refluxed under Dean-Stark trap conditions for 6 h. The mixture was cooled to room temperature, extracted with saturated aqueous sodium bicarbonate, and the organic phase separated, d?ed and concentrated in vacuo. The clean crude bromoindene (4.6 g, 100%) was isolated as an oil and used in the next step without purification. This bromoindene (4.5 g) was diluted into (1 : 1) methanol-methylene chloride (150 mL), chilled to -78 0C, and treated with ozone for 30 minutes, removed from the ozonator, warmed to room temperature, and treated with solid sodium bicarbonate (2.5 g) and dimethylsulfide (3 mL). The reaction mixture was aged for 14 h, treated with 78% ammonium hydroxide in water (30 mL), and the mixture maintained at room temperature overnight. The reaction mixture was then concentrated in vacuo, re-dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, and the organic phase separated, dried and concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage, SiO2, 20% EtOAc-heptane) to provide the solid bromoisoqumolme. EXAMPLE 59 was prepared from this bromoisoqumohne by first Heck coupling in a similar manner as described in EXAMPLE 53 above and illustrated in Scheme 8. The resultant lsoquinohne acrylamide methyl ester intermediate was saponified with LiOH, and the acid reduced with p-toluenesulfonyl hydrazide, both in a similar manner as described in the examples above to provide the desired product. LCMS m/z 321 (M++ 1)

Statistics shows that 34598-50-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,3-dihydro-1H-inden-1-ol.

Reference:
Patent; MERCK & CO., INC.; WO2006/52555; (2006); A2;,
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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 2043-47-2, name is 1H,1H,2H,2H-Nonafluoro-1-hexanol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1H,1H,2H,2H-Nonafluoro-1-hexanol

To a solution of the perfluoroalkyl alcohol (10 mmol) in 10 mLof dry THF, was added sodium hydride (60% 1.4 equiv. dissolved in 2 mL of dry THF in oil) at 0 C under nitrogen atmosphere. The mixture was stirred for 30 min. Then 1.35 g (10 mmol) of henylisothiocyanate was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride. The aqueous layer was washed with diethyl ether and the combined organic layers were dried over Na2SO4. The solvent was removed by vacuum evaporation and the crude products were purified with column chromatography on silica gel (70-230 meshes) using petroleum ether/diethyl ether (8:2) as eluent or recrystallized in cyclohexane to give the corresponding O-perfluoroalkyl thiocarbamate.

With the rapid development of chemical substances, we look forward to future research findings about 2043-47-2.

Reference:
Article; Chniti, Ines; Sanhoury; Chehidi; Journal of Fluorine Chemistry; vol. 156; (2013); p. 101 – 105;,
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Related Products of 2425-28-7 , The common heterocyclic compound, 2425-28-7, name is 2-Bromo-1-phenylethan-1-ol, molecular formula is C8H9BrO, 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.

Under room temperature, in DMSO to the proper amount of organic solvent, by adding 100mmol compounds represented by the following general formula (I) compound, 200mmol aboving (II) compound, 20mmol catalyst (to 5mmol1 – (1-ferrocene amido ethyl) – 3-isopropyl-1-imidazole Iodized salt and 15mmolCu (OTf)2(triflic acid copper) mixture), 240mmol oxydizers PhI (OAc)2, 100mmol alkali DBU and 25mmol accelerator CeCl3, then heating up to 70 C, and at this temperature the stirring reaction 5 hours;After the reaction, the reaction solution is filtered, filtrate under stirring the pH value adjusted to neutral, and then fully saturated salt water for washing, chloroform extraction 2-3 time, combined with the phase, is distilled under reduced pressure, the resulting residue over silica gel column chromatography, to volume ratio of 1:2 of the mixed solution of petroleum ether and ethyl acetate to elute, collect eluant and evaporating eliminates takes elution solvent, thereby obtaining the compound (III) variety, the yield is 95.8%.

The synthetic route of 2425-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yang Xiujuan; Yang, Xiujuan; (9 pag.)CN105503672; (2016); A;,
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Synthetic Route of 25392-41-0, Adding some certain compound to certain chemical reactions, such as: 25392-41-0, name is 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one,molecular formula is C10H7ClO3, 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 25392-41-0.

Take the above crude product (2g, 9.50mmol) in a 200ml single-necked flask.Add 1N NaOH solution (100ml),The solution immediately turns thick yellow,The above solution was placed in an oil bath and heated at reflux for 2 h.After the reaction,Cool to room temperatureThe pH was adjusted to 2-3 with concentrated sulfuric acid, and the resulting solution was extracted with ethyl acetate (30 ml x 4).Combine the organic phase,Wash with saturated brine (20ml x 2)Drying with anhydrous sodium sulfate,filter,The filtrate was evaporated under reduced pressure to give a tan brown columnar crystal of 1.3 g, and the crude yield was 71.2%.The above crude product (1 g, 5.20 mmol) was suspended in 10 ml of methanol.0.5ml concentrated sulfuric acid was added dropwiseAfter dripping, the temperature is increased to reflux for about 4 hours.After the reaction,Remove methanol under reduced pressureThe residual liquid is poured into 30 ml of water,Extract with ethyl acetate (20ml×3)Combine the organic phase,Wash with saturated sodium bicarbonate solution (15ml×2)Saturated brine (15ml x 2) washes,Drying with anhydrous sodium sulfate,filter,The filtrate was evaporated under reduced pressure to give a tan oil.Column chromatography (petroleum ether/ethyl acetate, 80:20, v/v) gave 0.75 g of a pale yellow solid in 70% yield.

According to the analysis of related databases, 25392-41-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Huang Wenlong; Qian Hai; Li Zheng; Wang Xuekun; Jiao Lei; Qiu Qianqian; (29 pag.)CN105017242; (2018); B;,
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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. 4654-39-1, name is 2-(4-Bromophenyl)ethanol, molecular formula is C8H9BrO, 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. Formula: C8H9BrO

A mixture of 2-(4-bromophenyl)ethan-1-ol (60 g, 300 mmol), BISPIN (84 g, 330 mmol), KOAc (90 g, 900 mmol) and PdC (dppf) (6.6 g, 9 mmol) in 1 ,4-dioxane (600 ml) was stirred under N2at 85C for 16 h. The RM was cooled to RT, filtered, the filtrate was concentrated and the residue purified by chromatography on silica gel eluting with EtOAc in petroleum ether (from 0 to 30%) to afford of the title compound as an oil (100 g).Method J: Rt = 1.87 min, [M+NH4]+= 266.

With the rapid development of chemical substances, we look forward to future research findings about 4654-39-1.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; HEBACH, Christina; HOLLINGWORTH, Gregory John; HOLZER, Philipp; IMBACH-WEESE, Patricia; LORBER, Julien; MACHAUER, Rainer; SCHMIEDEBERG, Niko; VULPETTI, Anna; ZOLLER, Thomas; (178 pag.)WO2019/186343; (2019); A1;,
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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. 5333-42-6, name is 2-octyldodecan-1-ol. A new synthetic method of this compound is introduced below., COA of Formula: C20H42O

2-octyldodecyl thiophene-3-carboxylate (SI). A solution of thiophene-3-carboxylic acid (1, 5.126 g, 40 mmol) in 150 mL DCM was stirred at room temperature under N2. Then 4-Dimethylaminopyridine (1.466 g, 12 mmol), a DCM solution of Nu,Nu’-dicyclohexylcarbodiimide ( 9904 mg , 48 mmol ) and 2-octyldodecan-l-ol (2, 23.88 g, 80 mmol ) were added to the system. The reaction mixture was stirred for another 12 hours. 50 mL distilled water was added and the reaction mixture was filtered, diluted with hexane and washed with water and brine. The organic layer was dried over Na2S04, filtered and concentrated. Then the residue was purified with silica gel chromatography to provide pure product as transparent liquid (17.25 g, 92% yield). 1H NMR (400 MHz, CDC13) delta 8.08 (d, / = 1.7 Hz, 1H), 7.54 – 7.51 (m, 1H), 7.31 – 7.28 (m, 1H), 4.18 (d, / = 5.6 Hz, 2H), 1.74 (d, / = 4.4 Hz, 1H), 1.41 – 1.22 (m, 32H), 0.88 (t, / = 6.3 Hz, 6H). 13C NMR (101 MHz, CDC13) delta 163.13, 134.27, 132.57, 128.09, 126.07, 67.68, 37.63, 32.12, 32.11, 31.64, 30.15, 29.85, 29.80, 29.76, 29.55, 29.51, 26.96, 22.89, 22.88, 14.31. HRMS (MALDI+) Calcd for C25H4402S (M+): 408.3062, Found: 408.3080.

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, 5333-42-6, 2-octyldodecan-1-ol.

Reference:
Patent; THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY; YAN, He; LIU, Jing; (52 pag.)WO2017/223407; (2017); A1;,
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Synthetic Route of 149104-89-2, 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. 149104-89-2, name is (4-Bromo-3-methylphenyl)methanol. A new synthetic method of this compound is introduced below.

Step 16: 1-bromo-4-(bromomethyl)-2-methylbenzeneTo a solution of (4-bromo-3-methylphenyl)methanol (5.15 g, 25.6 mmol) and NBS (9.07 g, 51.2 mmol) in DCM (100mL) was added drop wise PPh3 (13.36 g, 51.2 mmol) in DCM (50 mL) at rt and the reaction mixture was stirred for 15 mins at rt. Then, water (50 mL) was added and the organic layers were washed with water (100 mL x 2) and dried over anhydrous Na2S04. After the removal of solvent, the residue was purified with column chromatography to afford 1-bromo-4-(bromomethyl)-2-methylbenzene (4.15 g, 65 percent yield) as a colorless oil. 1H NMR (300MHz, CHLOROFORM-d) delta: 7.50 – 7.48 (d, 1 H), 7.26 (s, 1 H), 7.08 – 7.05 (m, 1 H), 4.41 (s, 2H), 2.39 (s, 3H),.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149104-89-2, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; JOHNS, Brian Alvin; SHOTWELL, John Brad; WO2012/67664; (2012); A1;,
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