Tag: M.W=200-300

Related Products of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Into a 1000-mL round -bottom flask was placed a solution of 4-(benzyloxy)phenol (5 g, 24.97 mmol, 1.00 equiv) in tetrahydrofuran (200 mL), 37 %NaOH (200 mL), and l-bromo-2- (2-bromoethoxy)ethane (57.5 g, 247.94 mmol, 10.00 equiv). The resulting solution was stirred overnight at 70 C in an oil bath. The reaction mixture was cooled. The resulting solution was extracted with dichloromethane and the organic layers were combined. The solution was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column (ethyl acetate/petroleum ether) to afford l-(benzyloxy)-4-[2-(2- bromoethoxy)ethoxy]benzene (6.67g, 76%) as a white solid. LC/MS (ESI) m/z: 350.05 [M+1] +.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARVINAS, INC.; QIAN, Yimin; CREW, Andrew, P.; CREWS, Craig, M.; DONG, Hanqing; HORNBERGER, Keith, R.; WANG, Jing; (606 pag.)WO2018/140809; (2018); A1;,
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These common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, 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. SDS of cas: 104197-14-0

To a solution of compound 5.2 (0.15 mL,1.22 mmol) in DME (7 mL) was added tetrakis triphenylphosphine palladium (78 mg,0.067 mmol). Stirring was continued at r.t. 5 min. 2-formyl phenyl boronic acid 5.1 (202 mg,1.35 mmol) and K2CO3 (745 mg,3.56 mmol) were added in turn. Stirring was continued at reflux 4h. The solvent was removed in vacuo. The crude was taken up with water and extracted with EtOAc (3 x 20 ml). The organic phase was washed with brine and dried over Na2S04. Flash chromatography purification (eluent PET/EtOAc) of the reaction crude afforded the title compound 5.3 (180 mg,0.72 mmol) as brownish oil.lH NMR (200 MHz,CDCI3) delta 4.20 (s,3H), 6.95 (d, / = 6.7 Hz,2H), 7.40 (d, / = 7.7 Hz,2H), 7.53 (d, / = 8.6 Hz,1H), 7.64-7.70 (m,1H), 8.03 (d, / = 7.8 Hz,1H), 10.02 (s,1H).

The synthetic route of 4-Bromo-2,6-difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TES PHARMA S.R.L.; PELLICCIARI, Roberto; (253 pag.)WO2018/69532; (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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-2-(2-bromoethoxy)ethane

a) Sodium hydroxide (50% w/w) (20.04 ml, 379.60 mmol) was added to (3R)-4-(2-chloro-6-(methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine (2.2 g, 7.59 mmol), 1-bromo-2-(2-bromoethoxy)ethane (3.79 ml, 30.37 mmol) and tetraoctylammonium bromide (0.415 g, 0.76 mmol) in methyl THF (20.05 ml). The resulting mixture was stirred at RT for 90 minutes. The reaction mixture was diluted with methyl THF (50 mL), and washed sequentially with water (50 ml) and saturated brine (5 ml). The organic layer was dried over MgSO4, filtered and then evaporated onto silica (30 g). The resulting powder was purified by flash chromatography on silica, eluting with a gradient of 0 to 5% MeOH in DCM. Pure fractions were evaporated to afford (3R)-4-(2-chloro-6-(4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl)pyrimidin-4-yl)-3-methylmorpholine (1.360 g, 50%); 1H NMR (400 MHz, DMSO-d6) 1.84-1.96 (1H, m), 2.02 (1H, td), 2.09 (3H, d), 2.27-2.45 (2H, m), 3.14 (1H, d), 3.10-3.26 (3H, m), 3.24 (1H, d), 3.33-3.41 (1H, m), 3.45 (1H, td), 3.60 (1H, dd), 3.71 (1H, d), 3.78-3.87 (1H, m), 3.87-3.97 (2H, m), 4.07 (1H, d), 4.32-4.48 (1H, m), 6.76 (1H, s); m/z: (ES+) MH+, 360.11 and 362.06.

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
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Reference of 24878-25-9, These common heterocyclic compound, 24878-25-9, name is 2,2′-Oxydianiline, 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.

L. Nicotinic acid acyl azide and bis(2-aminophenyl) ether were synthesized according to previous literatures [24-26], respectively. A solution of nicotinic acid acyl azide (1.04?g, 7.0?mmol) in toluene (30?mL) was refluxed under nitrogen for 1.5?h, and bis(2-aminophenyl) ether (0.60?g, 3.0?mmol) in acetonitrile (30?mL) was added dropwise. The mixture was stirred for another 1.5?h and cooled to room temperature. The precipitate that formed was collected by filtration and purified by recrystallization from CH3OH/DMF(V: V?=?2:1) to give a white solid. Yield: 1.07?g, 81%; mp: 285???286?C. 1H NMR (DMSO-d6, 400?MHz): delta 6.84 (d, 2H, J?=?7.6?Hz, Ar-H), 7.02 (t, 2H, J?=?5.2?Hz, Ar-H), 7.18 (t, 2H, J?=?5.6?Hz, Ar-H), 7.36 (dd, 2H, J?=?2.8?Hz, Ar-H), 7.99 (m, 2H, Py-H), 8.23 (d, J?=?2.8?Hz, 2H, Py-H), 8.35 (d, J?=?6.8?Hz, 2H, Py-H), 8.61 (s, 2H, Py-H), 8.75 (s, 2H, CONH), 9.52 (s, 2H, CONH). 13C NMR (DMSO-d6, 400?MHz): delta 152.98, 145.76, 143.53, 140.33, 136.81, 131.60, 125.47, 124.64, 124.15, 123.20, 120.23, 118.38. Anal. Calcd(%) for C24H20N6O3: C 65.45, H 4.58, N 19.08; found(%): C 65.49, H 4.62, N 19.03. FT-IR (KBr pellet, nu/cm-1): 3344 (m, NH), 1715 (s, CO), 1599 (s, NH). ESI-MS: m/z?=?441 [M+H]+, 463 [M+Na]+.

The synthetic route of 24878-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Chao; Yi, Xian-Mei; Chen, Dong-Mei; Zhu, Bi-Xue; Inorganica Chimica Acta; vol. 476; (2018); p. 123 – 128;,
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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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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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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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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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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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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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