Month: August 2021

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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H9BrO

[00432] In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (22 mg; 0.027 mmol) and triethylamine (0.36 ml; 2.58 mmol) in dioxane (4 ml; dried over 4 ? sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (0.19 ml;, 1.31 mmol) and 4-bromodiphenyl ether (216 mg; 0.865 mmol) were added and the reaction mixture was stirred at 80 C. GC analysis after 18 h showed a peak at 13.84 mins which was identified by GC/MS as the desired compound.

The synthetic route of 101-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
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112970-44-2, name is 2-Bromo-3-methoxyaniline, 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. HPLC of Formula: C7H8BrNO

35% HCl (3 mL) and ice (3 g) were added to 2-bromo-3-methoxyphenylamine (0.83 g, 4.11 mmol) obtainedin Step A, and cooled to 0-5C. NaNO2 (0.31 g, 4.52 mmol)/H2O (2 mL) solution was slowly added thereto, and themixture was stirred at 0-5C for 20 minutes. Pre-prepared KI (6.82 g, 41.1 mmol)/H2O (10 mL) solution was slowly addeddropwise to the reaction solution, and the reaction was carried out at room temperature for 12 hours. After terminationof the reaction, NaOH solution was added thereto, and the reaction solution was extracted with DCM. The organic layerwas washed with saturated NaHCO3 aqueous solution and water. The extracted organic layer was concentrated underreduced pressure and purified by column chromatography (eluent, EtOAc/Hex = 1/10) to obtain the title compound (0.88g, 68 %).1H NMR (500 MHz, CDCl3) delta 7.48(d, 1H), 7.00(dd, 1H), 6.85(d, 1H), 3.87(s, 3H)

The synthetic route of 112970-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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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. 458-50-4, name is 4-Bromo-3-fluoroanisole, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-fluoroanisole

Step 2: 9-(2-Fluoro-4-methoxy-phenyl)-bicyclo[3.3.1]nonan-9-oll-Bromo-2-fluoro-4-methoxy-benzene (4.10 g, 20 mmol) was dissolved in THF (30 ml) and cooled to -78°C. To the solution was added n-BuLi (1.6 M in THF, 12.5 ml, 20 mmol) dropwise. The reaction mixture was stirred at -78°C for 20 min, after which bicyclo[3.3.1]nonan-9-one (2.76 g, 20 mmol) in THF (20 ml) was added dropwise. The reaction mixture was stirred at -78°C for 2.5 hours and quenched at the same temperature with aqueous NH4C1 solution. Water and EtOAc were added. The reaction mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2S04). Silica gel chromatography (EtO Ac/heptane) provided 3.4 g of the title compound.Ci6H2iF02 (264.15), LCMS (EI+): 264.14 (M+).1H NMR (CDCI3, 300MHz), delta 7.41 (t, 1H), 6.55-6.71 (m, 2H), 3.80 (s, 3H), 2.61 (br. s, 1H), 2.39 (m, 2H), 1.49-2.17 (m, 12H).

The synthetic route of 458-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; KOSLEY, Raymond Walter, Jr.; SHER, Rosy; NEUENSCHWANDER, Kent W.; GURUNIAN, Vieroslava; WO2011/34832; (2011); 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. 2944-49-2, name is 1-Methoxy-2,3-dimethylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 2944-49-2

Carbon tetrachloride (100 ml) will be 3 – methoxy ortho-xylene crude product dilution dissolved, added to the mixed liquid in the N – bromo succinimide (NBS, 34.0 g, 190.4 mmol) and 2,2′-azobisisobutyronitrile (AIBN, 0.30 g), after mixing the heated to 77 C stirring reflux 24 h. TLC detection reaction has been substantially completely, cooling stop stirring, filtering the reaction solution, saturated sodium bisulfite solution for fragrance (50 ml × 2) washing twice, static layering, the collection of organic phase, the organic phase dried with anhydrous sodium sulfate 12 h. Filtering, environment friendly with silica gel column chromatography, eluting agent is pure petroleum ether, to obtain white solid 7.70 g, yield 69.2%.

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; Ma Shutao; Jin Chaobin; Wang Yinhu; Gu Xinjie; (32 pag.)CN108929260; (2018); A;,
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Electric Literature of 450-88-4, A common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Intermediate Example Int10.101 -bromo-2-methoxy-4-(methy Isu Ifany l)benzeneTo a stirred solution of 1 -bromo-4-fluoro-2-methoxybenzene (4.0 g) in DMF (40 mL) was added sodium methanethiolate (2.76 g). The mixture was stirred at r.t. for 30 minutes and at 85 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 280 mg of the title compound.1H-NMR (400MHz, DMSO-d6): delta [ppm]= 2.46 (s, 3H), 3.82 (s, 3H), 6.74 (dd, 1 H), 6.91 (d, 1 H), 7.44 (d, 1 H). 1 -bromo-2-methoxy-4-(methy Isu Ifany l)benzene To a stirred solution of 1 -bromo-4-fluoro-2-methoxybenzene (10.0 g) in DMF (100 mL) was added sodium methanethiolate (4.44 g). The mixture was stirred at 65C for 2 h. The mixture was cooled to 0 C and methyl iodide (4.55 mL) was added. The mixture was stirred at r.t. for 1 h and further sodium methanethiolate (4.44 g) was added. The mixture was stirred at 65C for 1 h. The mixture was cooled to 0 C and methyl iodide (4.55 mL) was added. The mixture was stirred at r.t. for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 6.2 g of the title compound as a 2: 1 mixture with the starting material. The mixture was used for the next step without purification.

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
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Related Products of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2×). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2×). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
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Reference of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

tert-BuLi (12 mL of a 1.7 M solution, 20 mmol) was added dropwise to a solution of 4-bromo-N,N-dimethylaniline (2.00 g, 10 mmol) in THF (40 mL) at 78° C. The resulting solution was stirred at 78° C. for 1 hour and was then warmed to ambient temperature. Tellurium powder (1.28 g, 10 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 1 hour. 1-Bromo-3-phenoxypropane (2.04 g, 9.5 mmol) in 5 mL of THF was added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was filtered through Celite and the filter cake was washed with CH2Cl2 (50 mL). The filtrate was concentrated and the residue was partitioned between H2O (100 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with additional CH2Cl2 (3*25 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was then purified by column chromatography on silica gel eluted with 60percent CH2Cl2/hexanes to give 1.9 g (52percent) of 23b as an orange oil: 1H NMR (400 MHz, CDCl3) 7.63 (d, 2H, J=8.8 Hz), 7.24 (t, 2H, J=7.8), 6.91 (t, 1H, J=7.2), 6.84 (d, 2H, J=8.0 Hz), 6.54 (d, 2H, J=8.8 Hz), 3.97 (t, 2H, J=6.0 Hz), 2.94 (s, 6H), 2.90 (t, 2H, J=7.4 Hz), 2.20 (quint, 2H, J=6.8 Hz); 13C NMR (75 MHz, CDCl3) delta 158.9, 150.3, 141.2, 129.4, 120.6, 114.5, 113.4, 94.7, 68.7, 40.2, 31.2, 4.3; High Resolution MS (EI) m/z 385.0694 (Calcd for C17H21NO130 Te: 385.0681). Anal. Calcd for C17H21NOTe: C, 53.32; H, 5.53; N, 3.66. Found: C, 53.26; H, 5.61; N, 3.32.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Research Foundation of State University of New York; US2008/26027; (2008); 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. 1535-73-5, name is 3-Trifluoromethoxyaniline, A new synthetic method of this compound is introduced below., Safety of 3-Trifluoromethoxyaniline

General procedure: If not commercially available, the corresponding anilide derivative was prepared according tothe procedure from Marsais and coworkers.3 To the aniline derivative (10 mmol, 1.0 equiv.)dissolved in CH2Cl2 (20 mL) was added triethylamine (1.5 mL, 11 mmol, 1.1 equiv.).Pivaloyl chloride (1.5 mL, 12 mmol, 1.2 equiv.) was added dropwise at 0 °C and the mixturewas stirred for 5 h at room temperature. The reaction was quenched with ice coldNH4Cl (50 mL) and the aqueous phase extracted with CH2Cl2 (3 x 20 mL). The combinedorganic phases were washed with sat. NaHCO3 (3 x 30 mL), dried over MgSO4 andconcentrated under reduced pressure. Pure product was obtained by purification by flashcolumn chromatography with a mixture of pentane and ethyl acetate.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vasquez-Cespedes, Suhelen; Holtkamp, Michael; Karst, Uwe; Glorius, Frank; Synlett; vol. 28; 20; (2017); p. 2759 – 2764;,
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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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8F3NO

N-Cyano-N’-(3-methoxy-5-trifluoromethyl-phenyl)-O-phenylisourea To a solution of 3-methyloxy-5-trifluoromethylaniline (11 mmol, 2.10 g) in dichloromethane (25 ml), diphenylcyanocarbonimidate (10 mmol, 2.38 g) and triethylamine (11 mmol, 1.53 ml) were added. The reaction mixture was stirred under nitrogen for 16 h at room temperature. After concentration the residue was stirred with water, the water was decanted followed by concentration. The residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give 0.413 g of the title compound (12%); Mp 168.5-169.5 C.; 1 H-NMR (CDCl3): delta 3.83 (s, 3H), 7.00 (s, 1H), 7.14 (m, 3H), 7,23 (s, 1H), 7.32 (t, 1H), 7.43 ppm (t, 2H), 8.7 (br s, 1H). EI SP/MS: 335 (M+).

According to the analysis of related databases, 349-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Novo Nordisk A/S; US6147098; (2000); A;,
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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 1663-61-2 as follows. Quality Control of (Triethoxymethyl)benzene

General procedure: Method A (synthesis of imidazol-5(4H)-ones 7) ? The appropriate alpha-aminocarboxylic acid hydrazide 5 (10 mmol) was added to a mixture of triethyl orthoester (30 mmol), dry xylene (40 mL) and 0.12 g p-TsOH and kept under reflux until the disappearance of the starting hydrazide 5 was completed (2-20 h). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:3 v/v or MeOH/CHCl3, 1:4 v/v.

According to the analysis of related databases, 1663-61-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Jasiak, Karolina; Tetrahedron Letters; vol. 54; 35; (2013); p. 4637 – 4640;,
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