Month: July 2021

These common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, 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. name: 2-Bromo-4-methoxyaniline

General procedure: To a solution of 2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added aq. HCl (15 mL conc. HCl in 50 mL water), then the mixture was cooled to 0 °C, and it was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After addition, the reaction was kept at the temperature lower than 5 °C for 30 min and it was added a solution of (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL) and extracted with CH2Cl2.The organic phase was dried over MgSO4. After workup, the brown oily product was distilled to afford a pale-yellow.

The synthetic route of 2-Bromo-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
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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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 1663-61-2

General procedure: The starting hydrazide 4, 8e-i (10 mmol) was added to a mixture of the appropriate triethyl orthoester (10 mol) and 0.1 g p-TsOH in 20 mL of xylene and kept under reflux for 3 h (TLC). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane/AcOEt, 1:2 v/v) or crystallised from benzene/hexane mixture.

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

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Ejsmont, Krzysztof; Tetrahedron; vol. 67; 40; (2011); p. 7838 – 7845;,
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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. 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H4BrF3O

Into a 300-ml glass reaction vessel equipped with a stirring apparatus were placed 10.0 g (42 mmol) of 1-bromo-2-(trifluoromethoxy)benzene, 2.9 g (4.2 mmol) of dichlorobis(triphenylphosphine)palladium(II), 20.1 g (54 mmol) of 2-(tributyltin)thiophene, and 100 ml of toluene. The mixture was reacted at an internal temperature of about 100C for 4 hours. After the completion of the reaction, the solvent was concentrated, and then 300 ml of hexane was added to the reaction solution. Subsequently, the mixture was filtered through [silica gel: potassium carbonate = 90 : 10 (wt%)]. The filtrate was concentrated, and the concentrate was purified by column chromatography (hexane: 100 vol%), to provide 6.6 g of Compound (3-1) in the form of a pale yellow liquid. [0125] The properties of Compound (3-1) were as follows. 1H-NMR (400MHz; CDCl3); 7.09-7.14 (m, 1H), 7.27-7.37 (m, 3H), 7.37-7.41 (m, 1H), 7.41-7.44 (m, 1H), 7.63-7.70 (m, 1H)

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; UBE Industries, Ltd.; TOKITO, Shizuo; KUMAKI, Daisuke; SHIMA, Hidetaka; ODA, Hiroyuki; TANAKA, Yasuhiro; KAKITA, Kazuaki; MACHIDA, Toshikazu; YONEDA, Yasuhiro; OMATA, Youji; SHIMANO, Tetsuro; EP2829542; (2015); A1;,
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Application of 651734-54-2, 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 651734-54-2 as follows.

Pd2dba3 (224mg; 0.245 mmol) and BINAP (305 mg; 0.49 mmol) was added to a solution of intermediate 25 (2g; 4.9 mmol), 2,6-difluoro-3,5-dimethoxyaniline (1.39g; 7.35 mmol) and Cs2003 (4.79g; 14.69 mmol) in dioxane (60 mL). The reaction mixture was heated overnight at 80C. Then, it was poured onto cooled water and the aqueous layer was extracted with DCM. The organic layer was dried over MgSO4, filtered and the solvent was evaporated. The resulting residue was cristallized from DIPE to afford 1.90g of intermediate 26 (75%).MP = 2600C (Kofler)

According to the analysis of related databases, 651734-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PILATTE, Isabelle Noelle Constance; MEERPOEL, Lieven; PONCELET, Virginie Sophie; WO2014/174307; (2014); A1;,
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These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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. Formula: C7H8BrNO

To a solution of 4-bromo-3-methoxyaniline pe=”Bold”>16(6 g, 30.0 mmol) in dichloromethane (30 mL) was addedboron trichloride (1 N, 33.0 mL, 33.0 mmol) dropwise over30 min at 0 °C under N2. Acetonitrile (3.2 mL, 60.0 mmol)and aluminium chloride (4.4 g, 33.0 mmol) was added andthe mixture was stirred at 0 °C under N2 for 30 min and thestirred at 70 °C for 16 h. The resulting mixture was cooledto 0 °C and 2 N HCl was added to the solution and themixture was stirred at 70 °C for 1 h. It was cooled to RT andextracted with ethyl acetate. The combined organic layerswere washed with brine, dried over Na2SO4 and filtered. Itwas then concentrated and the residue was purified by silicagel column chromatography eluting with cyclohexane/EA(50:1) to give brown solid 17 (3.7 g, 50.7percent). 17: 1H NMR(300 MHz, CDCl3) delta 7.85 (s, 1 H), 6.48 (s, 2 H), 6.10 (s,1 H), 3.89 (s, 3 H), 2.53 (s, 3 H).

The synthetic route of 4-Bromo-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Jingyu; Du, Guoxin; Zhao, Yuanyuan; Zhang, Liuqiang; Li, Bo; Zhu, Weiliang; Huang, Cheng; Li, Yiming; Guo, Fujiang; Medicinal Chemistry Research; vol. 27; 7; (2018); p. 1851 – 1862;,
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Related Products of 104-92-7, 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. 104-92-7 name is 1-Bromo-4-methoxybenzene, This 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.

General procedure: n-BuLi (1.2 mmol) was added to a THF (6 ml) solution ofaryl bromide (1 mmol) at -78C. After stirring for 1 h at same temperature, a THF solution of MOM-Cl or BOM-Cl (1.1 mmolin 4 ml dry THF) was added dropwise to it. Stirring was continuedfor another 1 h at same temperature and slowlywarmed to 0C over another 1 h and quenched with saturatedaqueous ammonium chloride solution. The organic layerwas separated and aqueous layer was extracted with diethylether. The combined organic layer was dried (Na2SO4) andevaporated. Column chromatographic purification gave thedesired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Panda, Biswajit; Journal of the Indian Chemical Society; vol. 95; 8; (2018); p. 981 – 985;,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5961-59-1

Example 1: Key Intermediate (S)-N-(1-(4-methoxyphenyl)(methyl)amino)-1-carbonyl-3-phenyl-2-yl)propynamide (4 Preparation of The starting material Boc-L-phenylalanine (1) (8.75 mmol, 2.3 g) was added to 15 mL of anhydrous dichloromethane solution. To this solution was then added 1H-benzotriazol-1-yloxytripyrrolidinylhexafluorophosphate (10.9 mmol, 5.7 g). After stirring for 0.5 h under ice bath, N,N-diisopropylethylamine (21.87 mmol, 3.61 mL) and N-methyl-4-aminoanisole (7.29 mmol, 1.0 g) were added to remove the ice bath. Stir at room temperature for 12 h. After the reaction is completed, the solvent is distilled off under reduced pressure, then saturated sodium bicarbonate solution is added to the bottle residue, and ethyl acetate is extracted; the organic layer is separated, 1N HCl solution is added, and ethyl acetate is extracted; the organic layers are combined and saturated. The brine was washed and the organic phase was dried over anhydrous sodium sulfate; Filtration and evaporation of the solvent under reduced pressure gave the intermediate compound tert-butyl-(S)-(1-((4-methoxyphenyl)(methyl)amino)-1-oxo-3-phenylpropyl- 2-Carboxylic acid (2) Crude 2.63 g, yellow oil, 94% yield,

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; Shandong University; Zhan Peng; Wu Gaoshan; Liu Xinyong; Li Guoxiong; Kang Dongwei; Yu Ji; Sun Lin; (25 pag.)CN108033952; (2018); A;,
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Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 4-Bromo-3-methoxyaniline

To a solution of 1 -bromo-4-isothiocyanato-2-methoxybenzene (0.46 g, 1.884 mmol) in methanol (5 mL) was added methanolic ammonia (2.0 M, 4.7). The resulting mixture was sirred at rt for 4 h. The crude mixture was concentrated in vacuo. The solid was dried under high vacuum to afford 0.49 g ( 100 percent yield) the titled compound as a white solid. LC-MS (M+H)+ 263.0. 1H NMR (400 MHz, methanol-^) delta ppm 7.48 (d, J=8.31 Hz5 1 H) 7.21 (br. s., 1 H) 6.78 (dd, J=8.31, 2.27 Hz, 1 H) 3.85 (s, 3 H). The product was used for subsequent chemistry without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
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Synthetic Route of 588-96-5, 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. 588-96-5 name is p-Bromophenetole, This 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.

General procedure: A 15 mL screw cap test tube was charged with Cu(OAc)2*H2O (20 mg, 0.1 mmol, 2 mol %), L4 (78 mg, 0.4 mmol, 8 mol %), hexane-2,5-dione (46 mg, 0.4 mmol, 8 mol %), KOH (650 mg, 10 mmol, 200 mol %), adipic acid (219 mg, 1.5 mmol, 30 mol %), NaOAc (246 mg, 3 mmol, 60 mol %), CTAB (182 mg, 0.5 mmol, 10 mol %), H2O (0.5 mL), aryl bromide (5 mmol) and amine (6.5 mmol, 130 mol %). Argon (flow rate 5-7 mL/min) was bubbled through the resulting mixture for 5 min. The reaction mixture was stirred in a closed test tube at 100C for 3-4 h until complete consumption of starting material as monitored by TLC (eluent-hexane), then cooled to room temperature and diluted with EtOAc (30 mL). The EtOAc solution was purified by flash-chromatography, washed with water (310 mL), and dried with anhydrous Na2SO4. Then EtOAc was evaporated under reduced pressure and the residue was recrystallized from hexane (substances 1-4) or aq EtOH (substances 5-9). In a case of the substances 5, 7-9 the residue was dissolved in diethyl ether. Aq HCl (37%) was added dropwise to the resulting solution until pH 3-4. The formed precipitate was filtered, washed with diethyl ether (10 mL) and dried at 50 C.

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

Reference:
Article; Kurandina; Eliseenkov; Khaibulova; Petrov; Boyarskiy; Tetrahedron; vol. 71; 41; (2015); p. 7931 – 7937;,
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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 stirred solution of pentane 1,5-diol 1 (11 g, 105.76 mmol) in N,N-dimethyl formamide (30 mL) was treated with 60 % of NaH (4.5 g, 116.34 mmol) at 0 C and stirred at room temperature for 30 min.1-bromo-2-ethoxyethane 2 (12 mL, 105.76 mmol) in N, N- dimethyl formamide (20 mL) was added to the above reaction mixture at 0 C and stirred at room temperature and stirred for 16 h under argon atmosphere. The reaction mixture was quenched with ice water (200 mL) and extracted with ethyl acetate (3 x 250 mL). Combined organic layers were washed with brine (2 x 100 mL) and dried over Na2SO4, evaporated under reduced pressure. Crude residue was purified by column chromatography (100-200 silica gel) using 30 % ethyl acetate in hexanes to afford 5-(2-ethoxyethoxy) pentan-1ol 3 (5.1 g, 28.97 mmol, 27 % yield) as an oily liquid. TLC system: 70 % ethyl acetate in hexanes – Rf: 0.50; LCMS: m/z = 199.12 (M+Na) +

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:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); A1;,
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