Author: Jessica.F

Synthetic Route of 207226-31-1, These common heterocyclic compound, 207226-31-1, name is 1,3-Dibromo-5-(trifluoromethoxy)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.

To a solution of 1,3-dibromo-5-(trifluoromethoxy)benzene (25 g, 78.15 mmol, 1 eq) in i-Pr2O (50 mL) was added n-BuLi (2.5 M, 32 mL, 1.02 eq) at -78C for 0.5 h, then acetone (7.9 g, 136 mmol, 10 mL, 1.74 eq) was added. The mixture was stirred at 20C for 2 h. The reaction mixture was poured into 100 mL of aqueous NH4Cl and the resulting mixture was stirred for 15 min. The organic phase was separated, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 80 g SepaFlash Silica Flash Column, Eluent of 0~1% Ethylacetate/Petroleum ethergradient 50 mL/min). The title compound (8 g, 26.75 mmol, 34% yield) was obtained as a yellow liquid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.94 (s, 6 H), 5.90 (s, 1 H), 7.91 – 8.01 (m, 2 H), 8.19 – 8.25 (m, 1 H).

The synthetic route of 207226-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
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Reference of 102-52-3,Some common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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 amixtureof5.0g (19.6 mmol) ofL-tryptophan methylesterand50 mLof methanol,6.0 mL(23.6 mmol) of 1,1,3,3-tetramethoxypropane wasadded. The reaction mixture wasadjusted pH 1-2 withHCl(5N) and stirred at 45 Cfor 48h. The mixture was evaporatedto dryness in vacuo, the residue wasdissolved in a mixture ofwater(30mL) and ethyl acetate (30mL),and the aqueousphasewas extracted with ethyl acetate (30mL×3). The organic phase wascombined, washed successively with 10%Na2CO3andsaturatedNaCl,dried over anhydrousNa2SO4, filtered, andevaporatedto dryness in vacuo. The residue was purified by chromatographyonsilica gel (Chloroform: Methanol, 30:1) toobtain5.4 g of the title compound as pale yellow oilin 88.5% yield.ESI-MS (m/e) 319 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,3,3-Tetramethoxypropane, its application will become more common.

Reference:
Article; Wu, Jianhui; Zhao, Ming; Wang, Yuji; Wang, Yaonan; Zhu, Haimei; Zhao, Shurui; Peng, Shiqi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 19; (2016); p. 4631 – 4636;,
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Related Products of 39021-83-5,Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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 magnetically stirred solution of 1 ,4-dimethoxy-2,3-dimethyl-benzene (13.90 g, 83.6 mmol) in carbon tetrachloride (300 mL) at room temperature was added N-bromo- succinimide (32.2 g, 176 mmol) in one portion, and the reaction mixture was heated up to 65C. Benzoyl peroxide (0.54 g, 2.23 mmol) was added at 65C, and the reaction mixture stirred for further 4 hours before cooling down to 55C. The reaction mixture was filtered, the solid washed with carbon tetrachloride, and the combined filtrates were concentrated in vacuo to yield 2,3-bis(bromomethyl)-1 ,4-dimethoxy-benzene (26.8 g, 82.7 mmol) in 99% yield.

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVERSYS AG; SCHNEIDER, Peter; RIEDL, Rainer; TIGGES, Marcel; GITZINGER, Marc; PIEREN, Michel; LEVI, Assaf; SEPHTON, Mark; SCHELLHORN, Birgit; ZUEGER, Patrik; BRAND, Michael; GYGAX, Daniel; SPIES, Peter; WO2014/118361; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, Product Details of 5414-19-7

(23a) A solution of methyl cyanoacetate (5.0 g, 50.6 mmol), 2-bromoethyl ether (16.9 g, 65.7 mmol), and potassium carbonate (17.5 g, 126.4 mmol) in acetone (100 mL) was heated at reflux overnight. The mixture was cooled, filtered, and concentrated to provide the desired pyran. The crude material was carried on as is.

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, 1-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
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Related Products of 60876-70-2,Some common heterocyclic compound, 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, molecular formula is C10H13BrO, 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 2 In a one-liter four-necked flask equipped with a stirrer and a reflux condenser, purged with nitrogen and dried was placed 24.3 g (1.0 mol.) of metallic magnesium flakes to which were added 10 ml of anhydrous diethyl ether and 2 ml of ethyl bromide. After confirming initiation of the reaction by bubbling on the surface of the metallic magnesium, a solution of 114.6 g (0.5 mol.) of p-tert-butoxybromobenzene in 400 ml of anhydrous diethyl ether was added dropwise at the refluxing temperature over approximately 1 hour, and stirring was continued for 5 hours to give p-tert-butoxyphenylmagnesium bromide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(tert-butoxy)benzene, its application will become more common.

Reference:
Patent; HOKKO CHEMICAL INDUSTRY CO., LTD; EP307106; (1989); 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. 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 63057-72-7

4-bromo-3-methoxyphenol 10 (19.8 mmol, 5.80 g) was dissolved infreshly distilled THF (200 mL) in an oven-dried three-neck flask underargon. Temperature was cooled down to -78 oC and the solution wasstirred for 30 minutes before dropwise addition of n-BuLi (1.6N in THF,21.8 mmol, 13.6 mL). Once the addition of n-BuLi was completed, themixture was stirred for another 30 minutes at -78 oC before the dropwise addition of freshlydistilled trimethyl borate (59.4 mmol, 6.75 mL) at this temperature. The reaction mixture wasallowed to warm at room temperature and stirred for 5 h. The temperature was cooled down to-20 oC and HCl 1N was slowly added to reach pH = 2-3. The reaction mixture was allowed towarm at room temperature and extracted three times with EtOAc. The organic layers werecombined, washed with brine, dried with MgSO4 and concentrated in vacuo until precipitationoccurred. An amount of hexanes was then added to maximize precipitation. The solution wasfiltered and the solid was filtered and dried under vacuum. The precipitation/filtration procedurewas repeated twice, yielding a total of 3.72 g (73%) of 4 as a white powder. mp = 184-189 oC.1H-NMR (500 MHz, CDCl3): delta = 4.02 (3H, s), 5.26 (2H, s), 7.01 (1H, d, J = 8.33), 7.31-7.50(5H, m), 7.77 (2H, dd, J = 7.78, 1.28). 13C-NMR (125 MHz, CDCl3): delta =56.05, 70.62, 112.97,117.98, 127.21, 127.96, 128.64, 129.71, 136.81, 149.06, 152.09. 11B-NMR (160 MHz, CDCl3): delta= 27.69. IR (NaCl): numax 1502, 1455, 1398, 1249, 1217, 1183, 1134, 1012, 846, 795, 746,697cm-1. HPLC (Retention time, %): 16.92 min, >99%. HRMS (ESI-TOF, m/z): calcd forC14H14BO3 (M-H2O+H)+ = 241.1033, found 241.1031.

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:
Article; Cardinal, Sebastien; Voyer, Normand; Tetrahedron Letters; vol. 54; 38; (2013); p. 5178 – 5180;,
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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. 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Product Details of 887581-09-1

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

The synthetic route of 887581-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Electric Literature of 36865-41-5, A common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 stirred solution of 3-hydroxy-4-methoxybenzaldehyde (40 g,0.17 mol) in MeCN (500 ml) were added 1-bromo-3-methoxypropane (32 g, 0.21 mol) andK2C03 (70 g, 0.51 mol). The mixture was refluxed overnight, cooled to room temperatureand quenched with H20, and extracted with Et0Ac(1 00 ml x 3). The combined organiclayers were washed with brine, dried over Na2S04, and concentrated to give crude 4-methoxy-3-(3-methoxypropoxy)benzaldehyde (50 g, 84% yield) as a white solid. LCMS(ESI) m/z: 225.3 (M + 1t.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
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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 16618-68-1 as follows. HPLC of Formula: C7H8BrNO

c) A solution of the compound of Example 374(b) (1 g, 4.78 mmol, 1.2 eq.), 3-bromo-5-methoxyaniline (0.8 g, 3.98 mmol) and potassium fluoride (0.23 g, 3.98 mmol, 1 eq.) in DMF was heated at 120 C. for 12 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 42% yield (0.81 g).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
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These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, 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. Product Details of 886762-08-9

Preparation F-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine.Pd2(dba)3 (1.1 g, 1.2 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (0.94 g, 2.4 mmol), 5- bromo-2-trifluoromethoxy-phenylamine (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1 M in THF, 288 mL) and N-methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 hours. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved in DCM (200 mL) and washed with H2O (1 x 100 mL). The organic phases were dried over anhydrous Na2S04, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 23 g of 4-(4-methyl-piperazin-1-yl)-2- trifluoromethoxy-phenylamine (70% yield) as a light brown powder.1H NMR (401 MHz, DMSO-d6) delta ppm 2.22 (s, 3H), 2.44 (t, J=4.88 Hz, 4H), 2.94 (t, J=4.88 Hz, 4 H) 4.77 (br.s., 2 H) 6.66-6.69 (m, 1 H) 6.73 – 6.80 (m, 2 H);MS calc: 276.1318; MS found: 276.1320

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; CALDARELLI, Marina; BERIA, Italo; COLOMBO, Nicoletta; PIUTTI, Claudia; SALSA, Matteo; TRAQUANDI, Gabriella; WO2012/13557; (2012); A1;,
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