Category: ethers-buliding-blocks

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. 27841-33-4, name is 4,5-Dimethoxybenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Quality Control of 4,5-Dimethoxybenzene-1,2-diamine

EXAMPLE XVII 6,7-Dimethoxy-3-methyl-3,4-dihydroquinoxalin-2(1H)-one 4,5-Dimethoxy-1,2-dinitrobenzene (34.2 g, 0.15 mol) was hydrogenated in 500 ml of methanol with Raney nickel catalysis using 1 atm hydrogen. After the calculated amount of hydrogen had been taken up, the process was stopped, the catalyst was removed by filtration with suction, and the solvent was stripped off in vacuo. To remove the water completely, the mixture was taken up twice in methanol and reconcentrated. 4,5-Dimethoxy-1,2-phenylenediamine (24.0 g), which remained as a brown oil, was refluxed for 48 hours in 200 ml of ethanol (96%) together with 17.1 ml (0.15 mol) of methyl 2-chloropropionate, with an addition of 21.0 ml (0.15 mol) of triethylamine. The solution, which was very dark, was concentrated, the concentrate was taken up in ethyl acetate, the mixture was washed twice with water and dried (sodium sulfate), and the solvent was stripped off in vacuo. The crude product was crystallized by stirring with diethyl ether (6.2 g, 19%). A analytically pure sample of melting point 151 C. was obtained by silica gel chromatography using ethyl acetate as the eluent. 1H NMR (60 MHz, d6-DMSO): delta=1.22 (d, J=7 Hz, 3 H), 3.63 (s, 3 H), 3.67 (s, 1 H), 3.6-3.7 (m, 1 H), 5.62 (br. s, 1 H), 6.40 (s, 1 H), 6.45 (s, 1H), 9.90 ppm (br. s, 1 H). MS: M+=222.

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; Aventis Pharma Deutschland GmbH; US6369057; (2002); B1;,
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These common heterocyclic compound, 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, 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. Safety of 1-Fluoro-3-(methoxymethoxy)benzene

To a solution of n-BuLi (76.85 ml, 192.122mmol, 1 eq) in THF (300ml) was added TMEDA (29.89 ml, 99.807 mmol, 1 .04 eq), the mixture was cooled to -78C and stirred for 1 h. Compound 2 (30g, 192.122 mmol, 1 eq) in THF (75ml) was added to it drop wise under argon, then reaction mass was stirred for 2hr at -78C, followed by addition of Trim ethyl borate at the same temperature. Then the mixture was slowly warmed to rt stirred for 16h. Then the reaction mass was cooled to 0C, then 30% H2O2 (18 ml) solution was added slowly drop wise. The reaction mass was warmed to rt and stirred at for 1 h. TLC analysis indicated formation of polar spot. The reaction mixture was dissolved in EtOAc (300ml) and washed with brine (2 x 50ml) & water (2x 50ml). 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 gel100-200mesh) using 8%petroleum ether as an eluent to give compound 3 ( 25g, 75.55% ) as a colorless oil.

The synthetic route of 1-Fluoro-3-(methoxymethoxy)benzene has been constantly updated, and we look forward to future research findings.

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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Synthetic Route of 166530-78-5, 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. 166530-78-5, name is (5-Bromo-2-methoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2-methoxybenzaldehyde 11 (1 g, 4.65 mmol) and hydroxylaminehydrochloride (388 mg, 5.58 mmol) in ethanol (2.8 mL) was stirred for 1 h at room temperature.Subsequently, hydrochloric acid (12 M, 1.6 mL, 18.6 mmol) and zinc dust (760 mg, 11.62 mmol)slowly were added to the solution and the mixture was stirred at room temperature for 15 min. Asolution of ammonia (30%, 2.8 mL) and sodium hydroxide (6 M, 2.8 mL) was added dropwise tothe resulting slurry, and the mixture was stirred at room temperature for 15 min. Then, theresultant solution was extracted with CH2Cl2, dried over anhydrous sodium sulfate, and filtered.The solvent was removed under vacuum to afford the crude benzyl amine. The residue wasdissolved in CH2Cl2 (20 mL) which was then followed by the addition of Boc2O (1.52 g, 7.0mmol) and Et3N (710 mg, 7.0 mmol) at rt, the mixture was stirred for 2 h. After completion ofthe reaction, water was added into it, organic phase was separated and aqueous layer wasextracted with CH2Cl2 (3 × 20 mL). Organic phases were combined, washed with brine, driedover anhyd.Na2SO4 and concentrated to get crude boc-amine, which was then purified by columnchromatography (100-200 mesh size) using ethyl acetate:pet ether (1:9) as an eluent to affordpure boc-protected benzyl amine 12 (1.47 g).

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

Reference:
Article; Lalwani, Komal G.; Sudalai, Arumugam; Synlett; vol. 27; 9; (2016); p. 1339 – 1343;,
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Electric Literature of 13353-03-2,Some common heterocyclic compound, 13353-03-2, name is 2,4,6,8-Tetraoxanonane, molecular formula is C5H12O4, 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.

To 250ml four-necked flask was added under mechanical stirring phenol (phenol and paraformaldehyde dimethyl ether molar ratio of 15:1), phosphoric acid (the molar ratio of phosphoric acid to paraformaldehyde dimethyl ether is 6.4: 1) and water (molar ratio of water and paraformaldehyde dimethyl etherRatio of 14: 1), the water bath was slowly heated to 80 C, and then 5 g of paraformaldehyde dimethyl ether was slowly added dropwise during the controlTemperature between 75 -85 C . Bi completed, maintaining the temperature at 80 C to continue the reaction 4h. Complete the reaction of raw materials, natural cooling to 45 C ,The reaction solution was poured into a separatory funnel, standing stratification, the lower phosphoric acid aqueous solution recovery applied. After the upper organic phase is neutralized by alkali,Concentrated under reduced pressure, the application of excess phenol recovery. The concentrate was diluted with ethyl acetate and washed successively with saturated aqueous ammonium chloride solutionWashed with water, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated to dry twice to obtain the crude product. Crude by high pressure liquid chromatographyMeasured, bisphenol F yield, selectivity and product distribution in Table 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6,8-Tetraoxanonane, its application will become more common.

Reference:
Patent; Yancheng Tonghai Biological Technology Co., Ltd.; Wang Hui; Shen Jianyi; Zhao Yupei; Zhu Jian; Wang Yang; (10 pag.)CN105152866; (2017); B;,
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Application of 10075-63-5,Some common heterocyclic compound, 10075-63-5, name is 1,5-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

1Og (0.05mol) of the 1,5-dimethoxynaphthalene, synthesized in PreparationExample 1-1, was dissolved in 160 ml of acetonitrile in a 1,000 ml round-bottom flask. A solution of 21g (0.12mol) of N-bromosuccinimide (NBS) in 180ml of acetonitrile was droplet added to the flask with stirring. After stirring at room temperature for 3 hours, the vacuum filtration of the reaction mixture formed precipitates which were washed with acetonitrile and then twice with hexane and dried to give 12.7 g of the title compound as white power. The properties of the product are as described below.[112][113] Yield: 69.02%, m.p.: 187-188 0C[114] Rf: 0.20 [hexane:ethylacetate(50: 1)][115] IH-NMR (CDCl , 400MHz): delta 7.68(d, J=8.4Hz, 2H), 6.72(d, J=8.4Hz, 2H), 3.91(s,6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; WO2008/18645; (2008); A1;,
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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. 706-27-4, name is 4-(Trifluoromethoxy)toluene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H7F3O

Example 38 6-Trifluoromethoxy-1H-indole Combine 1-methyl-4-trifluoromethoxybenzene (5.44 g, 30.87 mmol) and H2SO4 (96%, 30.9 ml). Cool to about 0C. Add dropwise fuming HNO3 (2.06 g, 32.72 mmol) while maintaining the temperature below 10C. When the addition is complete, warm to ambient temperature. After 2.5 hours, pour the mixture onto ice/water, extract with dichloromethane. Combine the organic extracts, wash with brine, dry (Na2SO4), then concentrate to residue. Chromatograph the residue on silica gel eluting with hexanes/ethyl acetate (75/25) to give, after evaporation, 1-methyl-2-nitro-4-trifluoromethoxybenzene: MS (ACPI): m/e 220.1 (M-1).

The synthetic route of 706-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; Chen, Zhaogen; Cohen, Michael Philip; Fisher, Matthew Joseph; Gillig, James Ronald; McCowan, Jefferson Ray; Miller, Shawn Christopher; Schaus, John Mehnert; Giethlen, Bruno; (141 pag.)EP1859798; (2015); B1;,
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Synthetic Route of 14093-86-8, The chemical industry reduces the impact on the environment during synthesis 14093-86-8, name is 1-Methoxy-2-methylnaphthalene, I believe this compound will play a more active role in future production and life.

Example 1 In a four-necked, round-bottomed flask fitted with a stirrer, a thermometer, a cooler and a dropping funnel, were placed 0.5 g of potassium ferricyanide, 17.2 g of 1-methoxy-2-methylnaphthalene (90% content), 10 ml of water and 100 ml of glacial acetic acid. The mixture was heated with stirring, and dropping of 35% hydrogen peroxide was started when the internal temperature reached 55C, with the total amount (33 g) being added over a period of one hour. Stirring was further continued for four hours while maintaining the internal temperature within the range of 50 to 60C. High-performance liquid chromatography (HPLC) was used to confirm the consumption of 1-methoxy-2-methylnaphthalene. At the end of reaction, 200 ml of hot water (about 50C) was added and the resulting mixture was extracted twice with 200 ml each of isopropylether. To the combined extracts were added 200 ml of n-hexane and 5 g of activated charcoal, the mixture was stirred at 50C for 30 minutes, and the insoluble matters and activated charcoal were filtered off. The filtrate was dried over anhydrous magnesium sulfate and concentrated, giving 9.5 g (61.0%) of 2-methyl-1,4-naphthoquinone as yellow crystals. The purity was 98.8% when measured by HPLC (relative peak-area method; UV detection at 254 nm).

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

Reference:
Patent; Eisai Chemical Co., Ltd.; EP247513; (1991); B1;,
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Application of 172282-50-7,Some common heterocyclic compound, 172282-50-7, name is 4-(Difluoromethoxy)benzene-1,2-diamine, molecular formula is C7H8F2N2O, 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.

In a mechanical stirrer, Reflux condenser, the thermometer of the four-mouth flask, with lye:Sodium carbonate 6. 6 grams + 20 grams of tap water,Stirring to dissolve, slightly cooling, adding4-difluoromethoxy-o-phenylenediamine 34. 8 g,Stir for 20 min. Heated to 30 C,25-35 C20 g of carbon disulfide was added dropwise,Drop finished 30-40 C insulation condensation 6h,Continue to heat up to 60-70 C insulation 6h, cyclization is complete, add activated carbon decolorization,The filtrate was adjusted to pH 5-6 with sulfuric acid, filtered, washed, dried,5-difluoromethoxy-2-mercapto-1H-benzimidazole was obtained in an amount of 33.2 g,The yield was 95.4% based on 4-difluoromethoxy-o-phenylenediamine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Difluoromethoxy)benzene-1,2-diamine, its application will become more common.

Reference:
Patent; ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY; JIANGSU YUXIANG CHEMICAL CO., LTD; ZHANG, ZHIGUO; CHENG, YUNTAO; ZHONG, XUHUI; LI, QINGLONG; CHENG, HONGWEI; (6 pag.)CN103539746; (2016); B;,
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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. 17600-72-5, name is 1-Ethoxy-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 17600-72-5

10 g of the compound obtained in the preceding stage are cooled to -10 C., 21.84 ml of chlorosulfonic acid and then 13.68 g of phosphorus pentachloride are added dropwise and the mixture is left stirring at -5 C. for 1 hour. The reaction mixture is run onto 250 ml of ice and water and extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with the gradient of the cyclohexane/AcOEt mixture from 95/5 (v/v) to 85/15 (v/v). The expected compound is obtained, M.p.=93 C. 1H NMR: CDCl3 (250 MHz): delta (ppm): 1.55, t, 3H, 3.99, s, 3H, 4.23, q, 2H, 6.97-7.02, mt, 1H, 7.46-7.48, mt, 1H, 7.66-7.71, mt, 1H.

The synthetic route of 17600-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2011/59955; (2011); A1;,
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Reference of 104750-60-9, 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. 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-(2-hydroxy-5-methylphenoxy)-3-methoxybenzoic acid (18o). The bromination of p-cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection4 (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 H2O (20 mL). After 10 min, NaHSO3 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 conc. HCl (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDCl3) 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).

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

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.; (20 pag.)US9512105; (2016); B2;,
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