Month: March 2021

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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-(Benzyloxy)-3-bromobenzene

To a solution of 1-(benzyloxy)-3-bromobenzene (1.00 g) in 1,2-dimethoxyethane (15 mL) were added tris(dibenzylideneacetone)dipalladium(0) (180 mg), 2′-[dicyclohexylphosphino]-N,N-dimethylbiphenyl-2-amine (150 mg), piperidine (500 muL), and tripotassium phosphate (2.5 g) at room temperature, and the mixture was stirred at 110C for 21 hours. After the reaction mixture was cooled to room temperature, insolubles were separated by filtration and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 – 85/15) to obtain 1-[3-(benzyloxy)phenyl]piperidine (722 mg).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53087-13-1.

Reference:
Patent; Astellas Pharma Inc.; EP2194044; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, belongs to ethers-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 1017779-69-9, HPLC of Formula: C7H5F4NO

[0193j Step 1[0194j Corresponding amine (1 equiv.) and triethylamine (1.5 equiv.) was dissolved in CH2C12 (54 mM corresponding to amine) and stirred at -78 C. Triphosgene (0.45 equiv.) dissolved in CH2C12 (20 mM, corresponding triphosgene) was added dropwise at -78 C. The reaction was then warm to rt and was stirred for 30 mm. The reaction was cooled to 0 C. Corresponding piperidine (1.5 equiv.) and triethylamine (1.5 equiv.) dissolved in CH2C12 (54 mM, corresponding piperidine) was added slowly and the reaction was further stirred at rt for 12 h. The reaction was quenched with the addition of HC1 solution (2M). The organic layer was collected and the aqueous layer was further extracted with EtOAc (EtOAc: Aqueous layer 1:1) for three times. The combined organic layer was washed with sat. NaC1 solution. The organic layer was dried over anhydrous magnesium sulfate and was concentrated in vacuo. The product was used without further purification.[0277j The reaction was carried out according to synthetic pathway 2. The 3-fluoro-4- (trifluoromethoxy)aniline (109 mg, 559 jimol) was reacted with 1-(4-aminopiperidin-1-yl)-2- methylpropan-1-one (143 mg, 838 jimol). The product was purified by flash chromatography using ethyl acetate :hexane (7:3). The product was further purified by recrystallization using methanol and water.[0278j Yield: 150 mg, 383 jimol, 68.6% yield. Purity (H-NMR): 95%

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

Reference:
Patent; EICOSIS, LLC; HAMMOCK, Bruce, D.; LEE, Kin, Sing, Stephen; INCEOGLU, Ahmet, Bora; WO2015/148954; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H8Br2O

General procedure: In a round bottom flask fitted with amagnetic stirrer, 2-chloro-1H-benzimidazole, 3, (0.50 g, 3.3 mmol) was dissolved in DMSO (3mL) and then NaH (60%; 0.19 g, 4.9 mmol) was added at 0 C and stirred for 1h. Next, benzylbromide (0.67 g, 3.9 mmol) was added to the suspension and the reaction was stirred at rt for 12h. Ice-cold water (15 mL) was added to the mixture and resulting precipitate was collected viafiltration. The filtrate was washed with water and dried under vacuum to give desired product, 4,as a white solid (0.75 g, 88%). LCMS: RT = 2.69 min., >98% 215 and 254 nm, m/z = 243.0 [M+ H]+. 1H NMR (499 MHz, CDCl3) delta 7.68 (d, J = 7.4 Hz, 1H), 7.35 – 7.24 (m, 5H), 7.16 (d, J =6.8 Hz, 2H), 5.38 (s, 2H). 13C NMR (126 MHz, CDCl3) delta 141.33, 134.83, 128.99, 128.22, 126.76,123.53, 123.05, 119.18, 109.98, 47.94.

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sharma, Swagat H.; Pablo, Juan Lorenzo; Montesinos, Monica Suarez; Greka, Anna; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 155 – 159;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 54149-17-6, 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 54149-17-6 as follows.

To a solution of m-toluidine (lOg, 9.3mmol) in DMF (lOmL), 1-bromo-2-(2- methoxyethoxy)ethane (0.85g, 4.6mmol) and diisopropylamine (1.2g, 0.93mmol) was added. The mixture was heated to 100C for 4h. The mixture was diluted with ethyl acetate and water, and the layers were separated. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was then concentrated. The residue was purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (650mg, 66%) as an oil. ?H NMR (300 MHz, CDC13) oe 7.07 (t, J 7.5, 1H), 6.56 (d, J 7.5, 1H), 6.52 – 6.45 (m, 2H), 3.71 (t, J= 5.3, 2H), 3.67 – 3.62 (m, 2H), 3.60 – 3.52 (m, 2H), 3.31 (t, J= 5.3, 2H), 2.28 (s, 3H); ESI MS m/z 210 [M + Hj.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROMEGA CORPORATION; DUELLMAN, Sarah; ROBERS, Matthew, B.; WALKER, Joel, R.; ZHOU, Wenhui; ZIMPRICH, Chad; (230 pag.)WO2016/210294; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11BrO

Step 1: Preparation of 1-[2-(2-methoxy-phenyl)-ethyl]-piperidin-4-one [Show Image] A mixture of 4-piperidone hydrochloride monohydrate (2.0 g, 14.8 mmol), 2-methoxy phenyl ethyl bromide (2.5 g, 11.7 mmol) and anhydrous potassium carbonate (7.2 g, 52.1 mmol) was prepared in DMF (65 mL) and heated at 60 C for 2 hours. The reaction mixture was concentrated under vacuum. The residue was taken up with ethyl acetate and washed with brine. The organic layer was dried (Na2SO4) and concentrated under vacuum. After purification by flash chromatography on silica, the title compound was obtained as a yellow solid (1.1 g, 36 %). TLC: ethylacetate/hexane (5/5): Rf : 0.6. 1H NMR (DMSO-d6, 400 MHz): delta 7.21-7.14 (m, 2H), 6.84-6.75 (m, 2H), 3.83 (s, 3H), 2.84-2.80 (m, 6H), 2.72-2.64 (m, 2H), 2.46-2.43 (m, 4H).

According to the analysis of related databases, 36449-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ares Trading SA; EP2508526; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-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 1535-73-5, Product Details of 1535-73-5

General procedure: A mixture of B (1 mmol) and dichloromethane (10 ml) was stirred for 10 min, then EDCI (1.2 mmol) and HOBt (1.2 mmol) were added. Added the appropriate amine (1.2 mmol) into the mixed solution after 30 min and refluxed for 12 h. The reaction mixture was filtrated with water and then the filtrate was dried and evaporated. Purification by silica gel afforded C1-C27

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

Reference:
Article; Ni, Hai-Jun; Cheng, Hui-Jie; Ge, Wei-Wei; Lin, Meng-Xue; Li, Qing-Shan; Ruan, Ban-Feng; Letters in drug design and discovery; vol. 13; 6; (2016); p. 495 – 504;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1077-01-6, A common heterocyclic compound, 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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 ice cooling mixture of 3-fluoro – trifluoromethoxyphenyl (20g) was dissolved in 40 ml of concentrated sulfuric acid, with rapid stirringWas added portionwise potassium nitrate (28g), was stirred at 0oC 3 hours and stirred at room temperature overnight, the reaction solution was carefullyGo on into 1 kg ice, stirred for 30 minutes, extracted with ethyl acetate, dried over sodium sulfate, filtered, and the filtrate was evaporated, the residue was purified by column chromatography to give 12 g pale yellow liquid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shanghai Hansen Biological Pharmaceutical Co., Ltd.; Jiangsu Stockhausen Pharmaceutical Group Co., Ltd.; Sun, Xingyi; Wei, Mingsong; Cui, Yuanyuan; Tong, Chaolong; Zhang, Fujun; Bao, Rudi; Yu, Hongping; Xu, Yaochang; (41 pag.)CN105503827; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 588-63-6

General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 molpercent), NaI (37 mg, 0.25 mmol, 0.5 equiv), and OTMEDA (241 mg, 1.5 mmol, 3 equiv) in dry EtCMe2OH (4 mL),were added alkyl halide (0.5 mmol) and the phenylboronic acid (98mg, 0.8 mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 ¡ãC for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 ¡Á 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product( Tables 3 and 4).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 588-63-6.

Reference:
Article; Di Franco, Thomas; Boutin, Nicolas; Hu, Xile; Synthesis; vol. 45; 21; (2013); p. 2949 – 2958;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, 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. Recommanded Product: 437-82-1

Example 37This example illustrates the preparation of compound 101a according to the approach provided in Scheme 31. The general method is applicable to other compounds of the present invention. In this example, Rv is H and Rw is CD3. Scheme 31Preparation of (5-bromo-2-chlorophenyl)(3,5-difluoro-4-hydroxyphenyl)- methanone (96)To a solution of 5-bromo-2-chlorobenzoic acid (3.2 g, 13.5 mmol) in dichloromethane (40 mL), oxalyl dichloride (1.7 mL, 27.1 mmol) was added. Then N, N-dimethylformamide (50 muL) was added dropwise. After the vigorous evolution of gas ceased, the mixture was stirred at 250C overnight prior to removal of the volatiles under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and cooled to 0 C. Aluminum trichloride (2.7 g, 20.4 mmol) was added in portions, and the mixture was stirred for 10 minutes. Then l,3-difluoro-2- methoxybenzene (2.0 g, 13.8 mmol) was added, and the mixture was stirred at 0 0C for 2 hours. Then the reaction was allowed to warm to 25 C overnight. The reaction was quenched with ice-water (30 mL) and extracted with dichloromethane (2 x 20 mL). The combined organic layers were washed with sodium hydroxide (2 M), water, hydrochloric acid (10%), and brine prior to drying over sodium sulfate. Crude product was obtained after dichloromethane was removed under reduced pressure. The sample was dissolved in tetrahydrofuran/methanol/water (30 mL, v/v/v = 2:3:1), and lithium hydroxide monohydrate (700 mg) was added. The mixture was stirred for 1 hour at 25 0C. The solvent was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3 x 30 mL), and the extracts were washed with brine, dried over sodium sulfate, and concentrated to a crude product under reduced pressure. The residue was purified by silica column chromatography to give 1.46 g of white solid (30% yield, purity: 95%). 1H-NMR (CDCl3, 400 MHz): delta 7.59-7.62 (m, IH), 7.49-7.50 (m, IH), 7.36-7.42 (m, 3H); HPLC-MS method: Method 2, retention time 3.81 min; MS ES” (m/z): 345(M – I)”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 437-82-1, its application will become more common.

Reference:
Patent; THERACOS, INC.; SEED, Brian; LV, Binhua; ROBERGE, Jacques, Y.; CHEN, Yuanwei; PENG, Kun; DONG, Jiajia; XU, Baihua; DU, Jiyan; ZHANG, Lili; TANG, Xinxing; XU, Ge; FENG, Yan; XU, Min; WO2010/9243; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 592-55-2, 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 592-55-2 as follows.

To a solution of methyl 4-(hydroxymethyl)benzoate (500 mg, 3.0 mmol) and 2-bromoethyl ethyl ether (2.0 mL, 18 mmol) in dry DMF (25 mL) was added dropwise KHMDS (18 mL, 0.5 M in toluene, 9.0 mmol). After being stirred at 70 C was 2 h the mixture was treated with water and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over MgSO4. After evaporation the crude product was purified by flash chromatography (hexane/EtOAc 5:1) to give 10a in 49% yield (350 mg). EI-MS: m/z 238 (M+); 1H NMR: (CDCl3, 600 MHz) delta (ppm): 1.23 (t, J = 7.0 Hz, 3H), 3.55 (q, J = 7.0 Hz, 2H), 3.61-3.67 (m, 4H), 3.91 (s, 3H), 4.64 (s, 2H), 7.42 (m, 2H), 8.01 (m, 2H); 13C NMR: (CDCl3, 90 MHz) delta (ppm): 15.2, 52.0, 66.7, 69.9, 69.9, 72.6, 127.2, 129.3, 129.7, 143.7, 167.0; IR: (NaCl) nu (cm-1): 2868, 1692, 1426, 1292, 1119, 764.

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huber, Daniela; Loeber, Stefan; Huebner, Harald; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 455 – 466;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem