Tag: M.W=200-300

Electric Literature of 34598-50-0 ,Some common heterocyclic compound, 34598-50-0, molecular formula is C9H9BrO, 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.

5-Bromo-1-indanol (1.0 g, 4.7 mmol) of Step A was dissolved in thionyl chloride (10 mL). After stirring at room temperature for 2 hrs, the solution was concentrated under vacuum. The residue was taken up in DMF (10 mL). To the mixture were added tert-butyl (3S)-3-methylpiperazine-1-carboxylate (0.94 g, 4.7 mmol), NaI (2 g, 13 mmol) and triethylamine (1.5 mL, 10 mmol). The resulting solution was stirred at 70 C. overnight. After cooling to room temperature, water was added. The solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (50% EtOAc in hexane) provided two isomers. Isomer 1 (fast moving isomer): 0.36 g; MS calculated for C19H27BrN2O2 (M+H)+ 395; found 395.1, 397.0. Isomer 2 (slow moving isomer): 0.33 g; MS found 395.1, 397.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34598-50-0, its application will become more common.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
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Application of 2215-78-3, 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.2215-78-3, name is (4-Phenoxyphenyl)methanol, molecular formula is C13H12O2, molecular weight is 200.2332, as common compound, the synthetic route is as follows.

Under an argon atmosphere and dissolved in the above process resulting in 1 4-phenoxyphenylmethanol (122) (300 mg), DPPA (495 mg) in anhydrous DMF (2.7 mL). DBU the (274 mg) was added under ice cooling,the mixture was stirred for 2 hours, the mixture was further stirred for 24 hours at room temperature. Water was added to the reaction mixture, the reaction mixture was extracted with ethyl acetate (30 mL). The organic layer 2N aqueous hydrochloric acid (30 mL), washed with saturated brine (30 mL), dried over anhydrous sodiumsulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash columnchromatography (developing solvent nhexane:ethyl acetate = 50: 1) to give the title compound (103 mg, 30% yield) as acolorless oil.

Statistics shows that 2215-78-3 is playing an increasingly important role. we look forward to future research findings about (4-Phenoxyphenyl)methanol.

Reference:
Patent; Nagoya City University; Miyata, Naoki; Suzuki, Takayoshi; Ota, Yosuke; Ueda, Ryuzo; Ida, Shinsuke; Rie, Masaki; (47 pag.)JP5725475; (2015); B2;,
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Related Products of 55362-80-6, 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. 55362-80-6, name is 9-Bromononan-1-ol. A new synthetic method of this compound is introduced below.

9-Bromononan-1-ol (3 g. 13.4 mmol) was dissolved in dichloromethane (70 mL, 0.2M) and to this solution were added dimethyl sulfoxide (2.9 mL, 40.3 mmol) and diisopropylethylamine (7.0 mL, 40.3 mmol). The flask was then sealed under nitrogen and cooled to -15 C. Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes and the resulting mixture was stirred at temperature between -10 C. and -20 C. for 30 minutes. The reaction was then quenched by adding water and the layers were separated. The organic layer was washed with aqueous sodium bisulfate (1M*3) and brine (*1), and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as an amber oil (2.4 g 81% yield). 1H NMR (CDCl3, delta): 9.78 (s, 1H), 3.40 (t, 2H), 2.43 (t, 2H), 1.85 (m, 2H), 1.63 (m, 2H), 1.5-1.25 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55362-80-6, its application will become more common.

Reference:
Patent; Mammen, Mathai; Mischki, Trevor; Hughes, Adam; Ji, Yu-Hua; US2006/35933; (2006); A1;,
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Reference of 2043-47-2 ,Some common heterocyclic compound, 2043-47-2, molecular formula is C6H5F9O, 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 2In a 5-liter, four-necked glass reactor were placed 3 liters of methylene chloride, 7 g (69 mmol) of triethylamine, 81 g (764 mmol) of sodium carbonate, 100 g (379 mmol) of 3,3,4,4,5,5,6,6,6-nonafluorohexanol and 0.5 g of Sumilizer GM. Thereto was dropwise added 55 g (764 mmol) of acrylic acid. Then, 135 g (765 mmol) of benzenesulfonic acid chloride was added dropwise while the reaction temperature was kept at 40 C. or lower. After the completion of the dropwise addition, stirring was conducted at 30 C. for 2 hours to obtain a reaction mixture. At this point, the conversion was 88% and the selectivity was 99%. 400 ml of water was added to the reaction mixture. Stirring was conducted for 1 hour. Then, the reaction mixture was allowed to stand. An organic layer was separated from an aqueous layer. The organic layer was subjected to distillation under reduced pressure to remove methylene chloride. To the distillation residue obtained was added 2 liters of methylene chloride. There were further added 15 g (148 mmol) of triethylamine and 10 g (139 mmol) of acrylic acid. To the mixture was dropwise added 24 g (136 mmol) of benzenesulfonic acid chloride while the reaction temperature was kept at 40 C. or lower. After the completion of the dropwise addition, stirring was conducted for 2 hours while the temperature of reaction mixture was kept at 30 C. At this point, the conversion was 99% or more and the selectivity was 99%. 250 ml of water was added to the reaction mixture, followed by stirring for 30 minutes. The reaction mixture was allowed to stand. An organic layer was separated from an aqueous layer. The organic layer was washed two times each with 250 ml of water, after which the organic layer was subjected to distillation under reduced pressure to remove the methylene chloride contained therein. To the distillation residue obtained was added 0.5 g of a polymerization inhibitor, Sumilizer GM. The mixture was subjected to distillation under reduced pressure to obtain 101 g (317 mmol, yield: 84%) of 3,3,4,4,5,5,6,6,6-nonafluorohexyl acrylate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2043-47-2, its application will become more common.

Reference:
Patent; TOKUYAMA CORPORATION; DAIKIN INDUSTRIES, LTD.; US2009/23948; (2009); A1;,
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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. 101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, molecular formula is C17H16O3, 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. category: alcohols-buliding-blocks

1.00 g (2.0 mmol) of the naphthol compound (19) and the following propargyl alcohol compound 0.81 g (3.0 mmol) was dissolved in 50 ml of toluene, 0.02 g of camphorsulfonic acid was further added, and the mixture was stirred under heating reflux for 1 hour. After the reaction, the solvent was removed and purification by chromatography on silica gel gave 1.02 g of a white powdery product. The yield was 69%.

With the rapid development of chemical substances, we look forward to future research findings about 101597-25-5.

Reference:
Patent; Tokuyama Corporation; Izumi, Shinobu; Teranishi, Kazuhiro; Daikoku, Yusuke; Sando, Mitsuyoshi; (46 pag.)JP5721544; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 75476-86-7, 6-Bromo-2,3-dihydro-1H-inden-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, Formula: C9H9BrO, blongs to alcohols-buliding-blocks compound. Formula: C9H9BrO

To a solution of 6-bromo-2,3-dihydro-1 H-inden-1 -ol (12 g, 56.3 mmol) in 1 ,4-dioxane (100 mL) was added bis(pinacolato)diboron (18.59 g, 73.2 mmol), potassium acetate (13.82 g, 141 mmol) and the mixture was degassed with argon for 20 mm in a sealed tube. PdCI2(dppf) (2.060 g, 2.82 mmol) was added and the reaction mixture was stirred at 90 00 for 2 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate wasconcentrated under reduced pressure to afford a crude residue. The crude residue was purified by column chromatography using 20% ethyl acetate in n-hexane as eluent. The eluted fractions were concentrated under reduced pressure to afford the title compound (12 g, 82% yield). 1H NMR (400MHz, ODd3) 5 ppm = 7.88 (s, I H), 7.72 (d, J=7.7 Hz, 1 H), 7.28 (s, 1 H), 5.25 (br t, J=5.8 Hz, 1 H), 3.08 (ddd, J=5.0, 8.4, 16.4 Hz, 1 H), 2.88 – 2.78 (m, 1 H), 2.51 – 2.41 (m, 1 H), 2.01-1.91 (m, 1H), 1.68 (br s, 1H), 1.37-1.27 (m, 12H).

The synthetic route of 75476-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; KERNS, Jeffrey K.; YAN, Hongxing; CALLAHAN, James Francis; HEIGHTMAN, Thomas Daniel; BOEHM, Jeffrey Charles; WOOLFORD, Alison Jo-Anne; (250 pag.)WO2016/203401; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20017-67-8, 3,3-Diphenyl-1-propanol, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

To a stirred solution of difluoroacetic acid (5.00 g, 52.1 mmol) and 3,3- diphenyl-1-propanol (11.4 ml, 57.3 mmol, 1.10 eq) in diethyl ether (100 ml) is added [4-DIMETHYLAMINOPYRIDINE] (0.64 g, 5.21 mmol, 0. [01 EQ)] followed by [DIISOPROPYLCARBODIIMIDE] (6.56 g, 52.1 mmol, 1.0 [EQ).] The mixture is stirred at room temperature overnight. The precipitate is removed by vacuum filtration and washed with ether and the filtrate concentrated in vacuo. The residue is filtered through a plug of silica gel using 5% ether/hexanes eluent and the filtrate collected and concentrated. The resulting compound (14.40 g, 46.64 mmol) in xylenes (150 [ML)] is added Lawesson’s Reagent (24.1 g, 59.61 [MMOL).] The reaction mixture is heated at reflux overnight and then cooled to room temperature. A precipitate formed which is removed by vacuum filtration and washed with ethyl acetate. The filtrate is passed through a plug of silica gel and eluted with 5% ether/hexanes and concentrated to give the title compound [7. 1H NMR] (400 [MHZ),] CDC13) 8 2.47, 4.07, 4.24, 5.82, 7.23.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20017-67-8, 3,3-Diphenyl-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/2967; (2004); A1;,
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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. 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 7-Hydroxy-4-(trifluoromethyl)coumarin

General procedure: Substituted coumarin (a-e) (0.001 mol), substituted DHA (I, II)(0.001 mol) and anhydrous potassium carbonate (0.0011 mol) were added in 15 mL DMF and stirred for 5 h. After the completion of reaction, the mixture was poured in the water and extracted with ethyl acetate (50 mLx3). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The product was purified through column chromatography.

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, 575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin.

Reference:
Article; Yu, Haonan; Hou, Zhuang; Tian, Ye; Mou, Yanhua; Guo, Chun; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 434 – 449;,
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Related Products of 1667-12-5 , The common heterocyclic compound, 1667-12-5, name is 4,4′-Bis(hydroxymethyl)biphenyl, molecular formula is C14H14O2, 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.

To a solution of 4,4?-biphenyldimethanol (3.01 g, 14 mmol) in dry THF (30 mL) at 0 was addedwith stirring under N2 a solution containing PBr3 (0.9 mL, 9.48 mmol) in dry THF (5 mL). Afterstirring for 2.5 h at room temperature, water (50 mL) was added at 0 and the solution was furtherstirred for 30 min at room tempetarure. THF was removed, and the residue was extracted into ethylacetate. This solution was washed with brine, dried over MgSO4 and evaporated. The residue waspurified by recrystallization from ethyl acetate.Yield : 89%. 1H NMR (CDCl3, 270 MHz)delta 7.56 (d, J = 8.1 Hz, 4H), 7.46 (d, J = 8.1 Hz, 4H), 4.52 (s,4H).

The synthetic route of 1667-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakurai, Hiroya; Arai, Tatsuo; Bulletin of the Chemical Society of Japan; vol. 89; 8; (2016); p. 911 – 913;,
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Adding a certain compound to certain chemical reactions, such as: 75476-86-7, 6-Bromo-2,3-dihydro-1H-inden-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: 75476-86-7, blongs to alcohols-buliding-blocks compound. Recommanded Product: 75476-86-7

A suspension of 6-bromoindan-1-ol (240 mg, 1.1 mmol), potassium acetate (550 mg, 5.6 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl](430 mg, 1.7 mmol) in 1,4-doxane (3.3 mL) was first degassed with stream of nitrogen for ?5 min, then [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (92 mg, 0.11 mmol) was added and the mixture was heated to 90 C. overnight. The reaction mixture was then diluted with EtOAc, filtered through celite, and concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 25% EtOAc/hexanes to provide the desired product (256 mg, 87%). LC-MS calculated for C15H20BO2 (M+H-H2O)+: m/z=243.2. found 243.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75476-86-7, 6-Bromo-2,3-dihydro-1H-inden-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
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