Month: March 2021

Reference of 5467-58-3, These common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, 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 a nitrogen atmosphere,Add 1-bromo-4-methoxynaphthalene (42.4 mg, 0.18 mmol) to a 25 mL sealed tube.Dichloroethane 2.0 mL, N-trifluoromethoxy-2,6-dichloropyridine hexafluoroantimonate (101 mg, 0.22 mmol) was added at 80 C for 36 hours. After adding 1.0 mL of a saturated aqueous solution of sodium hydrogencarbonate and 8.0 mL of distilled water, it was extracted with dichloromethane (15 mL ¡Á 3), washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Filter and spin dry the solvent. Column chromatography gave 18.0 mg of 1-bromo-2-trifluoromethoxy-4-methoxynaphthalene in a yield of 31%. 10.8 mg of 1-bromo-3-trifluoromethoxy-4-Methoxynaphthalene, yield 19%. The total yield is 50%.

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Mei Benzhaoxiong; Zhou Min; Hu Jinbo; (18 pag.)CN105017143; (2018); B;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H11BrO

Step 2 To an acetonitrile (250 mL) solution of crude product 2 (24.5 g) obtained from Step 1, benzyl-2-bromoethylether A (27.3 mL, 173 mmol) and potassium carbonate (27.5 g, 199 mmol) were added, under nitrogen atmosphere, followed by heating at reflux for 4 hours and a half. The reaction solution was filtered and then the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate and concentrated in vacuo to yield crude product 3 (54.6 g). LC/MS (Method A): 1.97 min, [M+H]+ = 319.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi&Co., Ltd.; EP2327704; (2011); A1;,
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Synthetic Route of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Step 1: Methyl 2-(3-(benzyloxy)phenyl)-2-hydroxy-2-phenylacetate Magnesium turnings (40.9 g, 1.71 mol) were placed in the three necked round bottom flask under argon. Anhydrous THF (1800 mL) and crystals of iodine (6.18 g, 0.024 mol) were added then 1-(benzyloxy)-3-bromobenzene (384.69 g, 1.46 mol) was added in portions. The internal temperature rose to 60 C. and the reaction foamed. The reaction was stirred for 2.5 hours at reflux. In another flask, a solution of methyl benzylformate (200.00 g, 1.22 mol) in anhydrous THF (2000 mL) was cooled to -70 C. under argon and to this the Grignard reagent was added dropwise over 3 hours. The reaction was allowed to slowly warm to room temperature and stirred at this temperature for 18 hours. The reaction was quenched with ammonium chloride solution. Layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic fractions were washed with brine and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to afford an oil. The resultant oil was evaporated with hexane twice to afford a solid (473.15 g). The solid was refluxed with 4730 ml hexane (10 ml/g) for 5 min, then allowed to cool to room temperature and stirred for 1 hour, then filtered and washed with hexane to obtain 386.34 g (HPLC: 83.85%). The product was crystallized in 3930 ml iPrOH (13 ml/g). The mixture was milky at reflux, was filtered (solid: 5.85 g, HPLC: 95.95%) and the filtrate was allowed to crystallized for 18 hours. The resulting precipitate was stirred for 1.5 hour at 10 C., then filtered and washed with hexane to afford the title product (180.54 g, 42%). 1H NMR (400 MHz, DMSO-d6); delta 7.44-7.22 (m, 11H), 6.98-6.93 (m, 2H), 6.92-6.88 (m, 1H), 6.68 (s, 1H, OH), 5.05 (s, 2H), 3.70 (s, 3H).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3,5-dimethoxybenzene

Condensation reaction: in with a thermometer, condenser 250 ml bottle to join four 21.9g 5 – bromo – m dimethyl ether {melting point 62 – 66 C; appearance: white solid; nuclear magnetic:1H NMR (CDCl3, 400MHz) delta (ppm) data are as follows: 3.82 (s, 6H, CH3), 6.37 (t, 1H, Ar – H), 6.81 (d, 2H, Ar – H)}, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130 ml methyl tert-butyl ether, magnetic stirring, oil bath heating, when the temperature rises to 50 C and maintaining at 4 hours, after the reaction is cooled to ambient temperature, for 60 ml 10% hydrochloric acid aqueous solution washing the reaction liquid, water washed to neutral, the organic layer is distilled under reduced pressure to obtain 17.4g 5 – propenyl – m dimethyl ether {melting point 97 – 100 C; appearance: white solid; nuclear magnetic resonance:1

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Weifang Xian Da Chemical Co., Ltd.; Li Kai; Wang Guangyue; Yang Qiwei; Zou Yabo; (7 pag.)CN106748673; (2017); A;,
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These common heterocyclic compound, 538-86-3, name is (Methoxymethyl)benzene, 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. Quality Control of (Methoxymethyl)benzene

General procedure: The reactions were carried out a ~40 mL, Teflon-lined, stainlesssteelautoclave. AcOH (2 mL), TEMPO (0.25 mmol), HNO3 (0.25mmol), the appropriate benzylic methyl ether (0.5 mmol), andNH4OAc (1.5 mmol) were added sequentially to the autoclave.Subsequently, the autoclave was pressurized to 1 MPa with O2,and the reaction mixture was heated with magnetic stirring at50 ¡ãC for 20 h, then cooled to r.t. The mixture was then dilutedwith Et2O (15 mL) and H2O (5 mL), and adjusted to pH 7?8 with2 M aq NaOH. The two layers were separated, and the aqueouslayer was extracted with Et2O (3 ¡Á 15 mL). The organic layerswere combined, dried (Na2SO4), filtered, and concentrated to avolume of approximately 3 mL in a rotary evaporator. GC analysisof the concentrated organic phase, with biphenyl or 1,2,4,5-tetramethylbenzene as internal standard, provided the GC yieldof the product. The crude product in the concentrated organicphase from another parallel experiment was purified bycolumn chromatography [silica gel (200?300 mesh), EtOAc?PE].

The synthetic route of (Methoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinzhe; Ren, Yun-Lai; Ren, Fangping; Cheng, Xinqiang; Zhao, Shuang; Wang, Jianji; Synlett; vol. 29; 18; (2018); p. 2444 – 2448;,
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Synthetic Route of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

General procedure: The orthoester (1.5 equiv) was added to a mixture of the 2-aminobenzamide (1.0 equiv) in absoluteethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reaction was heated at reflux for 12?24 h.The reaction mixture was cooled and concentrated under vacuum. If the crude product was pure by1H-NMR, it was triturated with 5percent ether in pentane. If it was not pure, it was recrystallized fromethanol. In some cases, it was necessary to remove excess orthoester under high vacuum at 50 ¡ãC prior to purification. The following compounds were prepared:

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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Reference of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

General procedure: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, nucleotides and nucleic acids; vol. 33; 11; (2014); p. 709 – 729;,
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Electric Literature of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows.

The product of Part F (5.0 g, 10.6 mmol), 18-crown-6 (Aldrich, 0.5 g, catalytic amount), potassium carbonate (Aldrich, 4.4 g, 31.8 mmol), and bis(bromoethyl)ether (Aldrich, 4.9 g, 21.2 mmol) were slurried in N,N-dimethylformamide (20 ml) and stirred at 65 C. for 15 hr. Afterward, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3?100 ml). The organics were combined and washed with water (twice), washed with brine (twice), dried over Na2SO4, and concentrated for a tan oil. The oil was washed with hexanes, and then dried to afford a tan oil. The tan oil was recrystallized from methanol to afford the desired intermediate in the form of a white solid (2.5 g, 44% yield). 1H NMR and LCMS showed desired intermediate.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-bromoethoxy)ethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
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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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Methoxy-4-(methoxymethyl)benzene

General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 muL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0-6.0 M in decane, 10.9 muL, 0.6 mmol) and themixture was stirred and heated at 50 C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25% aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83% yield.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; 13; (2017); p. 1576 – 1580;,
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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. 92248-06-1, name is Bis(3-methoxyphenyl)amine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

(3) The third step: under argon protection, add to the double-mouth bottle4,4 ‘, 4 “, 4” -tetrabromostatrene,3,3’-dimethoxydianiline, palladium acetate, sodium tert-butoxide and tri-tert-butylphosphine, adding 5 mL of toluene, stirring and placing at 130 C., reacting for 12 hours, stopping the reaction, adding saturated chlorinated The ammonium solution was extracted three times with dichloromethane and the organic layer was dried over anhydrous MgSO4. The crude product was subjected to silica gel column chromatography (petroleum ether: dichloromethane = 2: 3, v / v)A yellow solid was obtained,Recrystallization from tetrahydrofuran / petroleum ether. The product TPE-OMe-mm, the product of the formula as shown in formula (VI):

The synthetic route of 92248-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Shao Guang; Kuang Daibin; He Yanjian; Chen Jian; (17 pag.)CN105037179; (2017); B;,
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