Month: July 2021

Synthetic Route of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Synthesis of 1-(4-methoxy-2-methylphenyl)propan-2-one (C8) Four batches of this experiment were carried out (4*250 g substrate). Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-yl acetate (187 g, 1.87 mol), palladium(II) acetate (7.5 g, 33 mmol) and tris(2-methylphenyl)phosphane (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 C. for 18 hours. After cooling to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 C. The resulting mixture was diluted with toluene (500 mL) and filtered through Celite; the filter pad was thoroughly washed with ethyl acetate (2*1.5 L). The organic phase from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield: 602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 7.05 (d, J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (s, 3H), 3.65 (s, 2H), 2.22 (s, 3H), 2.14 (s, 3H).

The synthetic route of 1-Bromo-4-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
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Reference of 2688-84-8,Some common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, molecular formula is C12H11NO, 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.

A solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40% hydrobromic acid (50 ml) at 0 C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40% hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5% hydrochloric acid, 10% potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45%) was obtained by column purification of the crude intermediate using pet ether as eluent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Phenoxyaniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2008/15237; (2008); A1;,
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Synthetic Route of 64465-53-8, 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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Fluoro-3-methoxyaniline (0.5 g, 3.55 mmol) in suspension in glacial acetic acid (15ml) is treated with a concentrated HCI (5 ml). The resulting solution is then cooled approximately to 0 0C and treated dropwise with a solution of sodium nitrite (0.245 g, 3.55 mmol) in water (2 ml). After 10 minutes the reaction mixture is added to a stirred solution of SO2/AcOH/CuCI2/H2O (40 ml) (the preparation of the reagent is described below). The reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is then poured into water (250 ml) and extracted with ethyl acetate (3 x 100 ml). The combined organic layers are washed with water (2 x 100 ml) followed by brine (100 ml) and dried over MgSO4. After filtration the solvent is removed in vacuo to give the titled product which is used crude in the next step.Preparation of the reagent SO2/AcOH/CuCI2/H2O:According to the reported procedure (E. E. Gilbert, Synthesis 1969, 1-10, p6), glacial acetic acid (100 ml), vigorously stirred at room temperature, is treated by bubbling SO2 gas. Once a saturated solution is achieved (approximately 10 g per 100 ml), the solution is treated with copper (II) chloride (4 g) in water (5 ml). The resulting mixture is allowed to settle to give a green solution.

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/68418; (2007); 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. 104-92-7, name is 1-Bromo-4-methoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrO

General procedure: In a nitrogen filled glove box, PdCl2(CH3CN)2 (3.25mg, 0.010025mmol) and 2a (11.8mg, 0.0375mmol) or 2b (17.7mg, 0.0375mmol) were measured into a 1 dram vial containing a small stir bar. The vial was sealed with a screw cap and septum and removed from the glovebox before adding Cy2NMe (235muL, 1.10mmol), aryl halide (1.00mmol), alkyl acetylene (1.10mmol), and 1:1 water/acetonitrile (2mL). The reaction vial was placed in a preheated oil bath at 80C and stirred until it reached completion as determined by gas chromatography (2-12h). Upon completion, the reaction mixture was taken into diethyl ether, washed with brine solution, dried with anhydrous magnesium sulfate, and filtered. The excess organic solvent was removed under reduced pressure, and the crude residues were taken into methylene chloride and evaporated onto silica gel under reduced pressure. Once dry, the silica gel mixture was used in column chromatography.

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; Moore, Jane N.; Laskay, Nicholas M.; Duque, Kevin S.; Kelley, Steven P.; Rogers, Robin D.; Shaughnessy, Kevin H.; Journal of Organometallic Chemistry; vol. 777; (2015); p. 16 – 24;,
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Synthetic Route of 109-85-3, The chemical industry reduces the impact on the environment during synthesis 109-85-3, name is 2-Methoxyethylamine, I believe this compound will play a more active role in future production and life.

To a solution of 2,7-dichlorothiazolo[4,5-d]pyrimidin-5-amine 10 (0.10 g, 0.45 mmol) and triethylamine (69 mul, 0.50 mmol) in dioxane (3 ml) was added 2-methoxyethylamine (39 mul, 0.45 mmol). The reaction mixture was heated at 70 C for 2 h. After cooling, the volatiles were removed under reduced pressure. The crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 40:1) affording the title compound as a white solid (0.11 g, 94%). Mp 236-237 C. 1H NMR (300 MHz, DMSO, 25 C): delta = 9.09 (s, 1H, NH), 6.71 (s, 2H, NH2), 3.52 (br s, 4H, CH2), 3.29 (s, 3H, CH3) ppm. 13C NMR (75 MHz, DMSO, 25 C): delta =171.8, 170.8, 162.3, 149.4, 107.6, 69.8, 57.9, 43.8 ppm. HRMS: calcd for C8H9ClN4O2S [M+H]+ 260.01347, found 260.03656.

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, 2-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jang, Mi-Yeon; Jonghe, Steven De; Segers, Kenneth; Anne, Jozef; Herdewijn, Piet; Bioorganic and Medicinal Chemistry; vol. 19; 1; (2011); p. 702 – 714;,
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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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, 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: C8H8Br2O2

A flask containing 4,5-dibromoveratrole (500 mg, 1.69 mmol), 4-fluorophenylboronic acid (946 mg, 6.76 mmol), Pd(OAc)2 (38 mg, 0.169 mmol), XPhos (161 mg, 0.338 mmol), and K2CO3 (1.4 g, 10.1 mmol) was degassed and dioxane (10 mL) and H2O (5 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 10% EtOAc/hexane yielded product as a white solid (525 mg, 95% yield); 1H NMR (400 MHz) (CDCl3) delta 7.12-7.08 (m, 4H), 6.96-6.91 (m. 6H), 3.97 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 161.6 (JC,F=244 Hz), 148.4, 137.3 (JC,F=3 Hz), 132.1, 131.4 (JC,F=8 Hz), 114.9 (JC,F=21 Hz), 113.6.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
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Electric Literature of 31465-36-8, These common heterocyclic compound, 31465-36-8, name is 4-(4-Methoxyphenoxy)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.

General procedure: A mixture of a 3{1,1} (1.4 g, 5.53 mmol) and phenyl isothiocyanate (1.08 mL, 8.27 mmol) in anhyd DMF (8.0 mL) was stirred at room temperature for 6-7 h. Thereafter the reaction mixture was diluted with 50 mL H2O and extracted with EtOAc (4 x 20 mL). The combined organic layer was dried over anhyd Na2SO4, concentrated and the residue thus obtained was purified through silica-gel column chromatography using EtOAc-Hexanes (70-90:30-10, v/v) as eluent to yield 4{1,1,1} as a white solid (1.7 g, 80%).

The synthetic route of 31465-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mishra, Amita; Batchu, Harikrishna; Srivastava, Kumkum; Singh, Pratiksha; Shukla, Pravin K.; Batra, Sanjay; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1719 – 1723;,
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Related Products of 13321-74-9, 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. 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 1-bromo-2,5-dimethoxy-4-methylbenzene (12) (1.98 g, 8.58 mmol) and (R)-3-acryloyl-4-phenyloxazolidin-2-one (13) (1.86 g, 8.58 mmol) in MeCN/H2O (10:1, 40 mL) were added Pd(OAc)2 (192.58 mg, 0.86 mmol), (o-tol)3P (522 mg, 1.7 mmol), and Et3N (2.391 mL, 0.017 mmol) at rt, and allowed to warm to 80 C. After being stirred at the same temperature for 2 h, the resultant mixture was added water and CH2Cl2 and then extracted with CH2Cl2. The combined extracts were washed with brine, the residue upon workup was chromatographed on silica gel with hexane/AcOEt (4:1 v/v) as a eluent to give a enone 5 (2.564 g, 81%) as a yellow solid; inlMMLBox -5.17 (c 0.95 in CHCl3); mp 55.5-59.5 C; IR (neat) 2958, 1781, 1705, 1505, 1465, 1384, 1209, 1045 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.24 (3H, s), 3.82 (3H, s), 3.82 (3H, s), 4.31 (1H, dd, J=8.8 and 4.0 Hz), 4.73 (1H, t, J=8.8 Hz), 5.57 (1H, dd, J=8.8 and 4.0 Hz), 6.72 (1H, s), 7.02 (1H, s), 7.30-7.39 (5H, m), 7.93 (1H, d, J=16.0 Hz), 8.12 (1H, d, J=16.0 Hz); 13C NMR (100 MHz, CDCl3) delta 16.7 (CH3), 55.8 (CH3), 56.0 (CH3), 57.8 (CH3), 69.8 (CH2), 109.8 (CH), 114.4 (CH), 115.7 (CH), 121.1 (Cq), 125.9 (CH), 128.5 (CH), 129.0 (CH), 131.8 (Cq), 139.3 (Cq), 142.0 (CH), 151.7 (Cq), 153.0 (Cq), 153.9 (Cq), 165.2 (Cq); HRMS (ESI) calcd for C21H21NO5Na [M+Na]+ 390.1317, found 390.1310.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,5-dimethoxytoluene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Miyawaki, Akari; Osaka, Mayu; Kanematsu, Makoto; Yoshida, Masahiro; Shishido, Kozo; Tetrahedron; vol. 67; 35; (2011); p. 6753 – 6761;,
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Application of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

[0094] (a) In a 20 mL vial was added 3-fluoro-4-trifluoromethoxyaniline (150 mg, 0.769 mmol) in acetic acid (0.5 mL) at room temperature. Bromine (118 , 2.30 mmol, 3 eq.) was added and the reaction was stirred for several hours. Dichloromethane (2 mL) was added to break up the solidified reaction mixture, followed by more bromine (40 , 0.781 mmol, 1 eq.) addition. After stirring for another hour, dichloromethane was removed by gently blowing a stream of nitrogen to the reaction mixture. The solid was filtered and washed thoroughly with water and then dried under vacuum to give 2, 6-dibromo-3-fluoro-4- trifluoromethoxyaniline as a white solid (172 mg, 0.489 mmol, 64% 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; CHEMOCENTRYX, INC.; DAIRAGHI, Daniel; DRAGOLI, Dean, R.; KALISIAK, Jarek; LANGE, Christopher, W.; LELETI, Manmohan, Reddy; LI, Yandong; LUI, Rebecca, M.; MALI, Venkat, Reddy; MALATHONG, Viengkham; POWERS, Jay, P.; TANAKA, Hiroko; TAN, Joanne; WALTERS, Matthew, J.; YANG, Ju; ZHANG, Penglie; WO2015/84842; (2015); A1;,
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