Month: November 2020

134364-69-5, 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. 134364-69-5, name is 2,3-Difluoroanisole, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of l,2-difluoro-3-methoxybenzene (3.0 g, 21 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise tert-butyllithium (19 mL, 25 mmol, 1.3 M in n-pentane). The mixture was stirred at this temperature for 30 minutes, then NN- dimethylformamide (6.1 g, 83 mmol) was added dropwise at -70 C. The reaction was stirred at – 70 C for another 2 hours. On completion, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give compound B-168 (4.0 g, crude) as a yellow solid. LCMS (B): tR=0.661 min., (ES+) m/z (M+H)+ =173.1.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
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7025-06-1, The chemical industry reduces the impact on the environment during synthesis 7025-06-1, name is 1-Bromo-2-phenoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70¡ãC,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-phenoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Xue Zhi; Hymel, David; Burke, Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 20; (2016); p. 5009 – 5012;,
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402-07-3, 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 402-07-3 as follows.

To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
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Adding a certain compound to certain chemical reactions, such as: 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, 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 349-55-3, 349-55-3

EXAMPLE 124 4-(3-Methoxy-5-trifluoromethylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3-methoxy-5-trifluoromethylaniline (55 mg, 0.290 mmol) similar to Example 117 and isolated as a yellow solid (27 mg, 34%). 1H NMR (CDCl3): 9.65-9.64 (m, 1H), 8.75-8.70 (m, 2H), 7.46-7.41 (m, 2H), 7.36 (s, 1H), 7.31 (s, 1H), 7.00 (s, 1H), 6.93 (s, 1H), 3.91 (s, 3H).

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, 3-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
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101-84-8, The chemical industry reduces the impact on the environment during synthesis 101-84-8, name is Diphenyl oxide, I believe this compound will play a more active role in future production and life.

Example 1; Decabromodiphenyl ether – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 % w/w) ; bromine, 475 g; AlCl3,4.3 g; and ceramic beads (1.5-3.5 mm diameter), 814 g-A solution of diphenyl oxide (42.5 g, ) in 20 ml of solvent mixture was dropped into the flask during 70 minutes with stirring while keeping the temperature at 7- 13 C . The reaction mixture was refluxed for 4.5 hours, the flask was cooled and 55 ml of water was carefully added to destroy the catalyst. Excess bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 99.4 % decabromodiphenyl ether and 0.1 % nonabromodiphenyl ether (in the Examples sometimes abbreviated “Deca” and “Nona”, respectively). Particle size 7.1 microns (dg0) .; Example 2 (comparative); Decabromodiphenyl ether – Bromination without milling in a mixed solvent.; The procedure of Experiment 1 was repeated without the ceramic beads present. The product consisted of 94.1 % Deca and 5.8 % Nona. Particle size 98 microns (d90).; Example 3; Decabromodiphenyl ether- increasing the crystal size of milled Deca in a simulated reaction mixture after bromination and destruction of the catalyst.; The product of Example 1, having a particle size of 7.1 microns (dgo) and an assay of 99.4 %, was charged to a 1 liter flask followed by 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 %); 4.3 g AlCl3, 50 g of bromine and 50 ml of water to destroy the catalyst. The mixture was refluxed for 5.3 hours, cooled and bleached with bisulfite. The product was filtered, washed with water and dried. The particle size v/as 28.8 microns (dgo), had an assay of 99.7 % and was easily filtered.; Example 7; Decabromodiphenyl ether – Bromination of pre-milled Deca precursor; To a 2 liter jacketed reaction vessel equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 500 g of milled Deca (content 97.3 %, particle size 3.8 microns (d90) ) , 1945 g of solvent mixture, 444 g bromine and 22 g AICI3. The mixture was heated at reflux for 3.5 hours. Water, 260 ml, was added and the excess bromine was bleached with sodium bisulfite solution. To the thick slurry was added 150 ml of water. The mixture was filtered and the dried solid comprised 99.6 % Deca with particle size 38.5 microns (dgo).; Example 8; Decabromodiphenyl ether- Bromination of pre-milled Deca precursor on an industrial scale; A reactor vessel of 16 cubic meters capacity was charged with 7500 liters of solvent consisting of 12.6 % dichloromethane, 32.5 % bromochloromethane and 54.9 % dibromomethane . Aluminum chloride, 150 kg, 8 tons of pre- milled Deca (Deca content 97.9 % with particle size 14 microns (dg0) ) and 1000 kg of bromine were added. The mixture was heated at reflux for 8 hours and was then bleached with 1340 liters of 38 % sodium bisulfite solution. The upper aqueous solution was decanted and the mixture was washed with two 1200 liters portions of water. Sodium hydroxide, 20 %, was added to neutralize the mixture which was then centrifuged. The product was dried and was found to contain 99.3 % Deca with particle size 42 microns (d90).; Example 9; Decabromodiphenyl ethane – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 520 g of solvent mixture (DCM 6 %, CBM 20 %, and DBM 74 % ) ; bromine, 539 g; AlCl3, 9 g; and ceramic beads (1.5-3.5 mm diameter), 840 g.A 55 % solution of diphenyl ethane in DCM (91.1 g, ) was dropped into the flask during 30 minutes with stirring while keeping the temperature at 21-26 0C. The reaction mixture was refluxed for 6.7 hours, and 120 ml of water was carefully added to destroy the catalyst. Bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water and was neutralized with 20 % NaOH. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 91.4 % decabromodiphenyl ethane and 7.8 % nonabromodiphenyl ethane. Particle size was 6.1 microns (d90).; Example 10 (comparative); Decabromodiphenyl ethane – Bromination without milling in a mixed solvent.; The procedure of Example 9 was repeated without the ceramic beads present. The product comprised 80.6 % decabromodiphenyl ethane and 18.6 % nonabromodiphenyl ethane. Particle size 22 .microns (dgo).

The chemical industry reduces the impact on the environment during synthesis Diphenyl oxide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BROMINE COMPOUNDS LTD.; WO2008/26215; (2008); A2;,
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366-99-4, A common compound: 366-99-4, name is 3-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 4; Parallel Synthetic Method B, for Library II Compounds; Fifty mL (13.5 mmol) of the prepared (4,6-dichloro-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl) amine solution was divided equally (2 mL or 0.54 mmol each) among 25 barcoded, 40 mL scintillation vials. Individual solutions of each R2NHR (where R2 amine indicates Monomer 2 in Table 2, 0.542 mmol) and DIEA (77 mg /104 muL, 0.596 mmol) in 0.5 mL of CH3CN were prepared and added to the correspondingly labeled 40 mL vials. The resulting solutions were shaken on the J-KEM block overnight at room temperature and then placed in a freezer (about -14 ¡ã C.) without purification until the next reaction.; Example 5; Parallel Synthetic Method C, for Library III Compounds; In an oven-dried round bottom flask, a solution of cyanuric chloride (5.0 g, 27.1 mmol) in 1,4-dioxane (40 mL) was cooled to freezing in a CH3CN/dry ice bath. To this frozen solution was added 40 mL of CH3CN, followed by DIEA (3.85 g/5.19 mL, 29.8 mmol). A solution of 3-fluoro-p-anisidine (3.83 g, 27.1 mmol) in 10 mL of CH3CN was then added slowly via syringe. The reaction mixture was stirred at about -20¡ã C. for about 1h and allowed to warm to room temperature over 1 h. The resulting 2-amino-4,6-dichlorotriazine solution was carried to the next step without purification.

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, 3-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
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Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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. 35896-58-3

Compound 3 (0.32 g, 1.5 mmol) was dissolved in acetonitrile (2 mL), and an excess of asolution of K2S2O8 (1.6 g, 6 mmol) in 3mL water was added at 25 C. The reactionmixture was stirred at room temperature for 1 h. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was extracted withdichloromethane (10mL 3). The organic layers were washed with brine until neutrality,then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude productwas purified by a silica-gel column chromatography with petroleum ether and EtOAc(3:1) to give CoQ0, 0.26 g, 96%, red needles, m.p 56-57 C (lit5 57-59 C). IR: (cm1)3590, 3415, 1661, 1603, 1291, 1226, 999. 1H NMR (400 MHz, CDCl3) d 6.44 (q,J1.7 Hz, 1H), 4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J1.6 Hz, 3H,CH3). 13C NMR (101 MHz, CDCl3) d 184.4 (C5O), 184.2(C5O), 145.0, 144.8, 144.0,131.2, 61.2 (OCH3), 61.1 (OCH3), 15.4 (CH3). GC-MS (EI): m/z 182. The spectroscopicdata are in accord with the literature

The chemical industry reduces the impact on the environment during synthesis 1,2,3,4-Tetramethoxy-5-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qiu, Yong-Fu; Yan, Yi-Yu; Lu, Bin; Tang, Lei; Zhai, Yu-Lin; Chen, Ke-Xin; Wang, Jin; Organic Preparations and Procedures International; vol. 51; 6; (2019); p. 602 – 605;,
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A common compound: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 60792-79-2

[0329] In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min. A solution containing Boc20 (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2C12 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2- aminoethoxy)ethylcarbamate (850 mg, 74%).

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, 60792-79-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; BEMIS, Jean E.; VU, Chi B.; MILNE, Jill C.; JIROUSEK, Michael R.; DONOVAN, Joanne; WO2014/107730; (2014); A2;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 103291-07-2

Under a nitrogen atmosphere, 4-fluoro-3-methoxybromobenzene (163 mg) was added dropwise to a THF suspension of magnesium (23 mg) and iodine (catalytic amount). After heating under reflux,After stirring at room temperature for 30 minutes, {(5S) -2-oxo-5- (propan-2-yl) -3- [6- (trifluoromethyl) pyridin-3-yl] imidazolidin-1-yl} acetaldehyde A THF solution of (50 mg) was added dropwise. After stirring at room temperature for 2 hours,A saturated ammonium chloride aqueous solution was added, and the mixture was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by preparative HPLC.DMSO (2 mL) of the obtained product2-iodoxybenzoic acid (27 mg) was added to the solution,Stir overnight at room temperature. After adding water and filtering through Celite,The filtrate was extracted with chloroform. After concentrating the organic layer under reduced pressure,The residue was purified by PTLC (silica gel, hexane / ethyl acetate = 1: 1),The title compound (24 mg) was obtained.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co Ltd; Moriya, Minoru; Yamamoto, Shuji; Abe, Kimiyoshi; Ota, Hiroyuki; Sun, Ziang Min; Wakasugi, Daisuke; Araki, Hiroko; (49 pag.)JP2015/157764; (2015); A;,
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Adding some certain compound to certain chemical reactions, such as: 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, 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 3401-47-6. 3401-47-6

2-Methoxynaphthalene-1-thiol (compound 11r) was prepared as follows. (Preparation of (2-methoxynaphthalen-1-yl)magnesium bromide) A THF solution (8 mL) of 1-bromo-2-methoxynaphtalene (4 g, 16.87 mmol) was added, dropwise, to a THF slurry (17 mL) of magnesium turnings (533 g, 21.93 mmol) that had been previously activated through the addition of 1,2-dibromoethane (150 muL, 1.69 mmol). The flask was gently heated with a heat gun, while avoiding boiling. After 30 min, the flask was irradiated at rt in an ultrasonic cleaning bath for 2.5 h to afford a THF solution of the Grignard reagent. Elemental sulfur (0.757 g, 23.62 mmol) was added in one portion, under a N2 blanket, to the 0 C. solution of (2-methoxynaphtalen-1-yl)magnesium bromide (vide supra). After 30 min, lithium aluminum hydride powder (0.32 g, 8.44 mmol) was added in very small portions. After 30 min, the reaction was diluted with cold, aqueous, saturated NH4Cl (20 mL) and then aqueous citric acid 2M (5 mL). The mixture was extracted with dichloromethane (3¡Á30 mL) and, after the removal of volatiles, the resulting slightly yellow solid was partially dissolved with pentane. The pentane solution was cooled by immersion into a -78 C. cooling bath and after 5 min the temperature was raised to 0 C. After 15 min the solution was filtered to afford 3.01 g (94%) of compound 11r as a white crystalline solid: Mp 66-67 C. (lit. 65-68 C.). 1H NMR (400 MHz, Chloroform-d) delta 7.98 (dd, J=8.5, 0.9 Hz, 1H), 7.74 (d, J=8.2 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 7.49 (ddd, J=8.4, 6.8, 1.3 Hz, 1H), 7.34 (ddd, J=8.0, 6.8, 1.1 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 4.39 (s, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, Chloroform-d) delta 151.51, 132.01, 129.28, 128.43, 126.64, 126.28, 124.04, 123.98, 114.72, 112.71, 56.82; IR (ATR) 3052, 2937, 2838, 2579, 1506, 1265, 1247, 1075, 797, 767, 741 cm-1; HRMS calculated for C22H18O2S2 (disulfide) 401.0640. found 401.0648 (M+Na)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Bromo-2-methoxynaphthalene.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY GHOST; FLEMING, FRASER FERGUSSON; Lujan-Montelongo, Jesus Armando; US2015/239833; (2015); A1;,
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