Month: May 2021

Synthetic Route of 126940-10-1, 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. 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 2 (25 g, 130.2mmol, 1 .Oeq) in dry THF (250ml_) and dry cyclohexane (40ml_) was added sec-BuLi (121.82ml_, 195.3mmol, 1.5eq) drop wise at -78 C under argon. The mixture was stirred for 2h at the same temperature, then compound 3 (62ml_, 520.3mmol, 4. Oeq) was added with sitrring for 10mins at the same temperature. TLC analysis indicated formation of a polar spot then the reaction mass was quenched with satd. NH4CI solution; the reaction mixture was dissolved in ether (2X500mL) and washed with brine (2 x 200mL) & water (2x200mL). The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to give a crude product; which was purified by column chromatography (silica gel 100- 200mesh) using 1 % EtOAc petroleum ether as an eluent to give compound 4 ( 20g, 45.1 % ) as a pale yellow color liquid.

The chemical industry reduces the impact on the environment during synthesis 1-Fluoro-3-(methoxymethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; PRAKESCH, Michael; JOSEPH, Babu; MORIN, Justin-Alexander; (441 pag.)WO2019/153080; (2019); A1;,
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Related Products of 330-93-8, The chemical industry reduces the impact on the environment during synthesis 330-93-8, name is 4,4′-Oxybis(fluorobenzene), I believe this compound will play a more active role in future production and life.

Step 1 2-Bromo-l , 1 -dimethoxypropaneOMeBr[00297] A solution of propanal (12 5 mL, 170 mmol) m MeOH (85 mL) is stirred at rt and molecular sieves (3 A, powdered, 4 3 g) are added The mixture is heated at reflux, Br2 (8 8 mL, 170 mmol) is added dropwise over 30 mm and reflux is then continued for 4 5 h The mixture is stirred overnight at rt and K2CO3 (11 9 g, 86 mmol) is then added and the resulting slurry is stirred for 2 5 h This is filtered and the solid is washed with MeOH (20 mL) B?ne (100 mL) is added to the filtrate and the mixture is extracted with pentane (3 x 75 mL) The extracts are d?ed over MgSO4 and evaporated under reduced pressure to afford a pale yellow oil (16 0 g) which is not purified further

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, 4,4′-Oxybis(fluorobenzene), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
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35736-52-8, name is 2,4-Dibromo-5-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. Quality Control of 2,4-Dibromo-5-methoxyaniline

2,4-Dibromo-5-methoxyaniline (930 mg, 3.31 mmol) and paraformaldehyde (160 mg, 5.30 mmol) were dissolved in trifluoroacetic acid (30 mL). The reaction mixture was stirred under an argon atmosphere in dark for 48 h. The reaction mixture was then basified with a solution of concentrated ammonia (30 mL) in water (30 mL). A saturated sodium hydrogen carbonate solution (100 mL) was added and the aqueous mixture was extracted into dichloromethane (3×50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed (silica, dichloromethane) to afford (+/-)-18 (450 mg, 53%) as a pale off-white solid: mp 181-182 C; Rf (CH2Cl2) 0.22; IR (neat) numax 2938, 2895, 2848, 1604, 1486, 1442, 1420, 1247, 1195, 1082 cm-1; 1H NMR (400 MHz, CDCl3) delta 3.74 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.15-4.33 (m, 4H, CH2), 4.47 (d, J 17.0 Hz, 1H, CH2), 4.52 (d, J 17.0 Hz, 1H, CH2), 6.66 (s, 1H, ArH), 7.09 (s, 1H, ArH), 7.61 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) delta 54.1, 55.3, 56.2, 60.2, 66.5, 107.1, 108.3, 111.5, 114.7, 120.8, 125.5, 131.0, 134.6, 145.4, 147.4, 153.5, 155.0; Anal. Calcd for C17H15Br3N2O2.0.1 CH2Cl2: C 38.93; H 2.90; N 5.31. Found: C 38.85; H 2.73; N 5.06%.

The synthetic route of 35736-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Malik, Qasim M.; Ijaz, Sadia; Craig, Donald C.; Try, Andrew C.; Tetrahedron; vol. 67; 32; (2011); p. 5798 – 5805;,
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Adding a certain compound to certain chemical reactions, such as: 870563-60-3, name is (4-Fluoro-2-methoxyphenyl)methanamine, 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 870563-60-3, COA of Formula: C8H10FNO

General procedure: Spirothiazamenthane 3 (1.0 eq) was dissolved in toluene (0.1 M concentration) in a microwave vial and the solution was treated with amine (10 eq) and PTSA (20 mol %). This mixture was heated at 150 C using microwaves for 4 h. After cooling, the solvents were removed by evaporation and the resulting residue was taken up in 1:1 Et2O/2M NaOH. The layers were separated and the aqueous layer was extracted 2 × with Et2O. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting crude products were purified as described below. Variations in reaction conditions are also noted below.

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:
Article; Arns, Steve; Balgi, Aruna D.; Shimizu, Yoko; Pfeifer, Tom A.; Kumar, Nag; Shidmoossavee, Fahimeh S.; Sun, Sharon; Tai, Sheldon S.-H.; Agafitei, Olga; Jaquith, James B.; Bourque, Elyse; Niikura, Masahiro; Roberge, Michel; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 64 – 73;,
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68155-69-1, name is 1-Bromo-4-ethoxy-2-methylbenzene, 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. Quality Control of 1-Bromo-4-ethoxy-2-methylbenzene

Example 11 [Show Image] Synthesis of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[4-chloro-3-(4-ethoxy-2-methylbenzyl)phenyl]-1-thio-D-glucitol; Five drops of 1,2-dibromoethane were added to a mixture of magnesium (1.11 g, 45.7 mmol), 2-(5-bromo-2-chlorophenyl)-1,3-dioxolane (9.64 g, 36.5 mmol) and tetrahydrofuran (20 mL) and this mixture was heated to reflux for two hours. The reaction mixture was cooled to room temperature, and tetrahydrofuran (15 mL) of 2,3,4,6-tetra-0-benzyl-5-thio-D-glucono-1,5-lactone (10.14 g, 36.5 mmol) was added dropwise to this solution and stirred at room temperature for 30 minutes. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:1) to obtain a colorless amorphous 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolan-2-yl)phenyl]-5-thio-D-glucopyranose (11.81 g, 87percent). [Show Image] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.06 (s, 1H) 3.47 – 3.58 (m, 1H) 3.64 (dd, J=10.0, 2.9 Hz, 1H) 3.83 – 4.21 (m, 9H) 4.48 – 4.56 (m, 3 H) 4.66 (d, J=10.6 Hz, 1 H) 4.82 – 4.97 (m, 3 H) 6.15 (s, 1 H) 6.77 (dd, J=7.9, 1.5 Hz, 2 H) 7.08 – 7.21 (m, 5 H) 7.23 – 7.37 (m, 14 H) 7.55 (dd, J=8.4, 2.5 Hz, 1 H) 7:92 (d, J=2.5 Hz, 1 H). Then, 6M hydrochloric acid (120 mL) was added to a tetrahydrofuran (50 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolane-2-yl)phenyl]-5-thio-D-glucopyranose (6.01 g, 8.12 mmol) while ice-cooled, and stirred at room temperature for two days. The reaction mixture was added with an iced water and extracted with ethyl acetate and the organic phase was washed with a saturated sodium bicarbonate aqueous solution, brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain colorless amorphous 2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose (4.53 g, 80percent). [Show Image] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.14 (s, 1 H) 3.43 – 3.58 (m, 1 H) 3.63 (dd, J=10.0, 2.6 Hz, 1 H) 3.87 – 4.16 (m, 5 H) 4.45 – 4.72 (m, 4 H) 4.80 – 5.05 (m, 3 H) 6.73 (d, J=7.8 Hz, 2 H) 7.02 – 7.43 (m, 19 H) 7.74 (dd, J=8.4, 2.5 Hz, 1 H) 8.06 (d, J=2.5 Hz, 1 H) 10.39 (s, 1 H). Then, 2.6 M n-butylithium hexane solution (1.6 mL) was added to a mixture of 1-bromo-4-ethoxy-2-methylbenzene (0.94 g, 4 . 37 mmol) and tetrahydrofuran (12 mL) at -78°C. After stirred for one hour, the mixture was added with a tetrahydrofuran (10 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose(1.52.g, 2.18 mmol), and, further stirred for 20 minutes, and the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =2:1) to obtain 2,3,4,6-tetra-O-benzyl-1-C-{4-chloro-3-[(4-ethoxy-2-methylphenyl)(hydroxy)methyl]phenyl}-5-thio-D-glucopyranose (1.72 g, 95percent) as a yellow amorphous diastereomer mixture. Then, an acetonitrile (20 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-{4-chloro-3-[(4-ethoxy-2-methylphenyl)(hydroxy)methyl]phenyl}-5-thio-D-glucopyranose (1.72 g, 2.06 mmol) was added sequentially with Et3SiH (1.98 mL, 12.4 mmol) and BF3*Et2O (1.04 mL, 8.27 mmol) while cooled on ice. After stirred for one hour, the reaction mixture was warmed up to room temperature and stirred for three hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =5:1) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[4-chloro-3-(4-ethoxy-2-methylbenzyl)phenyl]-1-thio-D-glucitol (1.01 g, 61percent) as a colorless powder. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 2.14 (s, 3 H) 3.01 – 3.12 (m, 1 H) 3.48 (t, J=8.9 Hz, 1 H) 3.65 – 4.06 (m, 10 H) 4.46 – 4.61 (m, 4 H) 4.80 – 4.91 (m, 3 H) 6.58 (dd, J=8.2, 2.5 Hz, 1 H) 6.68 – 6.76 (m, 2 H) 6.81 (d, J=8.4 Hz, 1 H) 6.98 (d, J=2.2 Hz, 1 H) 7.10 – 7.39 (m, 21 H).

The synthetic route of 68155-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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Related Products of 887267-47-2, 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. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3-Bromo-5-(trifluoromethyl)aniline (2.5g, 10.4mmol), 1,4-diazabicyclo [2.2.2]octane (DABCO, 1.4g, 12.5mmol) was dissolved in toluene (40mL). Then 1.9mL carbon disulphide was added dropwise to the above mixture. Subsequently, the mixture was reacted at room temperature for 8h. The product was collected by filtration and dried under vacuum to afford 5 as slight yellow solid (1.2g, 40%).

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

Reference:
Article; Sun, Ying; Shan, Yuanyuan; Li, Chuansheng; Si, Ru; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 373 – 385;,
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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. 2338-54-7, name is 4-Fluoro-3-methylanisole, A new synthetic method of this compound is introduced below., COA of Formula: C8H9FO

6-Fluoro-3-methoxybenzoic acid 4-Fluoro-3-methylanisol (1.0 g, 7.1 mmol) was dissolved in a mixture of pyridine (16 mL) and water (32 mL). Potassium permanganate (3.4 g, 21 mmol) was added and the reaction mixture was refluxed for 3 h and then left at room temperature over night. After filtration and extraction with CH2 Cl2 the aqueous phase was acidified with HCl precipitating the product (440 mg). 1 NMR (CD3 OD): delta7.44-7.47 (m, 1H), 7.18-7.16 (m, 2H), 3.86 (s, 3H); 13 C NMR (CD3 OD): delta167.55, 158.35 (d, J=192 Hz), 156.30, 121.65 (d, J=8.7 Hz), 120.63 (d), 118.94 (d, J=24.4 Hz), 117.03, 56.59.

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; Aktiebolaget Astra; Cornell Research Foundation, Inc.; The University of Maryland at Baltimore; US5523475; (1996); A;,
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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. 10075-63-5, name is 1,5-Dimethoxynaphthalene, A new synthetic method of this compound is introduced below., Recommanded Product: 10075-63-5

70% Nitric acid (4.5 mL) in acetic acid (4.5 mL) was added slowly to a stirred suspension of 1,5-dimethoxynaphthalene(3.76 g, 20 mmol) in acetic acid (50 mL)at room temperature. Upon stirring overnight at ambienttemperature, the precipitate was filtered off,washed with water, recrystallized from methanol, anddried. Light yellow solid, yield 82%. 1H NMRspectrum, delta, ppm: 3.91 s (6H), 7.31 d (J = 8.5 Hz, 2H), 8.01 d (J = 8.5 Hz, 2H). 13C NMR spectrum, delta, ppm:57.45, 107.87, 116.85, 124.51, 140.69, 155.01.

The synthetic route of 10075-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong; Zhang; Huang; Meng; Li; Russian Journal of General Chemistry; vol. 87; 4; (2017); p. 837 – 841; Zh. Obshch. Khim.; vol. 87; 4; (2017); p. 837 – 841,5;,
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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. 456-55-3, name is (Trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H5F3O

Example 2 4-Chloromethyl-1-trifluoromethoxybenzene 200 g of trifluoromethoxybenzene and 48 g of paraformaldehyde were dissolved in 500 ml of methanol, and dry hydrogen chloride gas was introduced at 60 C. for 7 hours. The waste gases were, via a reflux condenser, passed into aqueous ammonia. The reaction mixture was then poured onto 1,000 g of ice and extracted twice with in each case 300 ml of methyl tert-butyl ether. The combined extracts were washed with 100 ml of water and then with 100 ml of sodium bicarbonate solution and subsequently concentrated. The residue was distilled at 18 hPa in a spinning band column. This gave 158.8 g of 4-chloromethyl-1-trifluoromethoxybenzene as a colorless liquid (65% of theory) of b.p. 71-74 C.

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; Marhold, Albrecht; Muller, Peter; US2002/82454; (2002); A1;,
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Synthetic Route of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

The bromination of p- cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection 4 (96% yield over two steps). A solution of bis(pinacolato)diborane (2.5 g), dioxane (40 mL), KOAc (2.5 g) and the aryl bromide (6.5 mmol) was purged with nitrogen before Pd(dppf)Cl2 (0.47 g) was added. The mixture was refluxed overnight. Silica chromatography (gradient to 20%) EtOAc/hexanes) gave the boronate ester (1.93 g), which was dissolved in acetone (20 mL) and treated with a solution of Oxone (4 g) in H20 (20 mL). After 10 min, NaHS03 was added and the resulting solution was extracted with EtOAc. Silica chromatography (gradient up to 15% EtOAc/hexanes) gave 2-(methoxymethoxy)-5-methylphenol (0.578 g, 53% over two steps). The diaryl ether was prepared from the phenol and appropriate 4-fluorobenzalde using General Procedure D. Silica chromatography (gradient up to 40% EtOAc/hexanes) gave the intermediate aldehyde (481 mg, 47%). The oxidation was followed by MOM cleavage with cone. HC1 (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDC13) delta 7.73-7.66 (m, 2H), 6.99-6.85 (m, 3H), 6.76 (s, 1H), 3.97 (s, 3H), 2.24 (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, 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; CARROLL, Frank, I.; THOMAS, James, B.; NAVARRO, Hernan, A.; MASCARELLA, S., Wayne; RUNYON, Scott, P.; JIN, Chunyang; KORMOS, Chad, M.; WO2013/86496; (2013); A2;,
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