Category: ethers-buliding-blocks

These common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, 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. Recommanded Product: 1-Bromo-2-phenoxybenzene

30 g of 1-bromo-2-phenoxybenzene was dissolved in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere,-78 ¡ã CRespectively.to the next,48 ml of 2.5 M-butyllithium was slowly added dropwise.After completion of the dropwise addition, stirring was performed for 30 minutes,2-Bromofluorene 31.2 gWas dissolved in 200 ml of absolute tetrahydrofuran and then slowly added dropwise.The reaction solution was maintained at -78 ¡ã C for about 1 hour, then warmed to room temperature and stirred for 12 hours.The reaction was terminated by adding diluted hydrochloric acid to the reaction solution, followed by liquid fraction extraction using methylene chloride.The obtained organic layer was dried with magnesium sulfate, filtered, and then distilled under reduced pressure. to the next,After adding 400 ml of acetic acid, a catalytic amount of hydrochloric acid was added dropwise, followed by stirring at a reflux temperature for 12 hours.After completion of the reaction, the reaction mixture was cooled to obtain a solid,After filtration, 32.0 g of compound AA was obtained by column chromatography.

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

Reference:
Patent; LG CHEM, LTD.; HONG, WAN PYO; KWON, HYOK JOON; KIM, KONG KYEOM; KIM, MIN JUN; KIM, SEONG SO; (79 pag.)KR2017/59910; (2017); A;,
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Related Products of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

1 Concentrated hydrochloric acid plus purified water (1) after dilution,Transfer to a 10L reactorWarm up to about 30C. Under nitrogen protection,The dimethylamino acetaldehyde diethyl acetal was slowly added dropwise to the diluted hydrochloric acid,About 2 hours after the addition,The reaction was stirred overnight at about 30C. MakeBefore use, neutralize to neutral with solid sodium carbonate,Inorganic salts are filtered away.

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

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yin Jianming; Lv Yubin; Li Bangliang; (13 pag.)CN107141261; (2017); 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 437-83-2 as follows. name: 3-Fluoro-2-methoxyaniline

A mixture of 3-fluoro-2-methoxyaniline (1.0 g, 7.1 mmol) and K2CO3 (1.04 g, 7.8 mmol) in DMF (15 mL) was added 1-bromobut-2-yne (981 mg, 7.1 mmol) was stirred at r.t. overnight. The resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-20% EtOAc in PE) to afford the title compound (552 mg, 40% yield) as a yellow oil. LC-MS (ESI): m/z (M+1) = 193.91.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK LIMITED; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WEATHERHEAD, Jason Gordon; (225 pag.)WO2017/93938; (2017); 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 4,4-Diethoxybutan-1-amine

To 0.95 g 1-isocyanatonaphthalene (5.62 mmol) dissolved in 20 cm3 of dry benzene 0.90 g 4,4-diethoxybutan-1-amine (5.59 mmol) was added. The mixture was stirred at room temperature for 12 h. The precipitate was filtered off,washed with 10 cm3 benzene, and dried in vacuum(0.01 torr, 4 h, r.t.) to give 6 as white solid. Yield 1.63 g(88%); m.p.: 121-122 C (from ethanol); 1H NMR[600 MHz, (CD3)2SO]: d = 1.11 (6H, t, J = 6.86 Hz,CH3), 1.48-1.52 (2H, m, CH2), 1.56-1.60 (2H, m, CH2),3.14-3.17 (2H, m, CH2), 3.42-3.47 (2H, m, CH2),3.55-3.60 (2H, m, CH2), 4.50 (1H, t, J = 5.49 Hz, CH),6.56 (1H, t, J = 5.48 Hz, NH), 7.41 (1H, t, J = 7.96 Hz,CHAr), 7.49-7.55 (3H, m, CHAr), 7.88 (1H, d,J = 8.23 Hz, CHAr), 7.99 (1H, d, J = 7.68 Hz, CHAr),8.08 (1H, d, J = 8.23 Hz, CHAr), 8.44 (1H, s, NH) ppm;13C NMR [150 MHz, (CD3)2SO]: d = 15.8, 25.6, 31.4,39.5, 61.1, 102.6, 116.9, 121.8, 122.4, 125.8, 126.0, 126.2,126.4, 128.8, 134.2, 135.7, 156.1 ppm; MS (MALDITOF):m/z = 353 ([M+Na]+).

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; Smolobochkin, Andrey V.; Gazizov, Almir S.; Voronina, Julia K.; Burilov, Alexander R.; Pudovik, Michail A.; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 535 – 541;,
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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. 62257-15-2, name is 2-Fluoro-5-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8FNO

2-Fluoronicotinic acid methyl ester (0.3 g, 1.934 mmol) and 2-fluoro-5-methoxyaniline(0.278 ml, 2.32 1 mmol) were heated by microwave irradiation at 130 C for 20 mm. SomeDCM was added and the mixture was washed twice with 1120. Organic phase was dried overNa2SO4, filtered and evaporated. Crude product was purified by trituration with diethylether. 0.324 g of the title compound was obtained.?H NMR (400 MHz, CDCJ3) oe ppm 3.82 (s, 3 H) 3.95 (s, 3 H) 6.49 (dt, 1 H) 6.78 (dd, I H) 7.03 (dd, I H) 8.27 (dd, I H) 8.33 (dd, I H) 8.42 (dd, 1 H) 10.42 (hr. s., I H).

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; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; VESALAINEN, Anniina; WO2015/144976; (2015); A1;,
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Electric Literature of 126829-31-0, The chemical industry reduces the impact on the environment during synthesis 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

Example 29; [0139] l,3-Bis(2,6-diisopropylphenyl)-4-(2,6-dimethoxyphenyl)-lH-l,2,3-triazolium hexafluorophosphate (lOal). To a stirred suspension of triazene 8a (3.66 g, 10 mmol), 2,6- dimethoxyphenylacetylene 91 (3.24 g, 20 mmol), and anhydrous potassiumhexafluorophosphate (1.84 g, 10 mmol) in dry dichloromethane (50 mL) in the dark at -78C is added tert-butyl hypochlorite (1.66 mL, 15 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to roomtemperature. The contents are then filtered, and the solid residue is washed withdichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. Ihour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt lOai as an off-white solid (5.25 g, 78%). Analytical samples were obtained after recrystallization by vapor diffusion of diethyl ether in an acetonitrile solution of lOai. 1H-NMR ((CD3)2SO, 300 MHz): delta = 10.03 (s, 1H), 7.79 (t, J = 7.9 Hz, 1H), 7.64-7.57 (m, 3H), 7.54 (t, J = 7.9 Hz, 1H), 7.42 (d, J = 7.9 Hz, 2H), 6.78 (d, J = 8.5 Hz, 2H), 3.71 (s, 6H), 2.43 (sept, J = 6.8 Hz, 2H), 2.29 (sept, J = 6.8 Hz, 2H), 1.27 (d, J = 6.8 Hz, 6H), 1.17 (d, J = 6.8 Hz, 6H), 1.08 (d, J = 6.8 Hz, 6H), 0.99 (d, J = 6.8 Hz, 6H). 13C-NMR ((CD3)2SO, 75 MHz): delta = 158.4, 145.2, 144.7, 139.9, 136.4, 135.2, 133.3, 132.9, 130.2, 129.2, 125.0, 124.8, 104.7, 98.0, 56.9, 28.8, 28.6, 25.8, 23.8, 23.1, 21.7. HR-MS (ESI): Calcd. for C34H44N302 [M+]: 526.3428, found 526.3433.

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-Ethynyl-1,3-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERTRAND, Guy; GUISADO-BARRIOS, Gregorio; BOUFFARD, Jean; DONNADIEU, Bruno; WO2011/139704; (2011); A2;,
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These common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, 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. Recommanded Product: 3-Methoxy-4-methylaniline

To 6.05 g of dichlorophenylborane dissolved in 40 ml of dichloromethane, at -20 C., are successively added 5.226 g of 3-methoxy-4-methylaniline dissolved in 50 ml of dichloromethane, and 13.4 ml of triethylamine dissolved in 25 ml of dichloromethane. After 30 minutes at -20 C., 5.412 g of 2,6-difluorobenzaldehyde dissolved in 60 ml of dichloromethane are introduced. After 24 hours at room temperature, the mixture is hydrolyzed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. To the oil obtained, dissolved in 80 ml of diethyl ether, are added 80 ml of 2 M sodium hydroxide solution and the mixture is left stirring for 18 hours. The phases are separated by settling and the organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with n-pentane to give 5.069 g of the expected product. 1H NMR delta in ppm (DMSO d6): 1.98 (s, 3H); 3.69 (s, 3H); 4.74 (s, 2H); 5.79 (d, 1H); 5.98 (d, 1H); 6.30 (s, 1H); 6.75 (s, 1H); 7.06 (m, 2H); 7.41 (m, 1H).

The synthetic route of 3-Methoxy-4-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2007/185136; (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. 101-84-8, name is Diphenyl oxide, A new synthetic method of this compound is introduced below., Recommanded Product: 101-84-8

(1) diphenyl ether (44.2 g, 0.26 mol) was added into a 250 ml four-necked flask and 123.5 g (1.25 mol) of dichloroethane was added and stirred for 1 hour.Cool to -5 ~ 0 ,Bromine (21 g, 0.13 mol) was rapidly added dropwise and stirred for 1 hour. The mixture was cooled to -5~0 C and 30% hydrogen peroxide (15 g, 0.13 mol)With 0.5 to 1 hour dropwise addition and termination,The temperature is controlled between 0 and 5 DEG C, naturally heated to 25 DEG C after dropping, incubated for 32 hours between 27 DEG C and quenched with 49g of 15% sodium bisulfite, after the phase separation,Then washed with water to neutral, to distill dichloroethane distillation, distillation under reduced pressure before recovery of diphenyl ether, and finally collected 4-bromo-diphenyl ether 51.7g, yield 80.0%, content of 98.2%.

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; Binhai Extensive Chemical Co., Ltd.; Wu Fucai; (8 pag.)CN106957220; (2017); A;,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Methoxy-N-methylaniline

4-Acetyl-N-(4-methoxy-phenyI)-N-methyl-benzamide 152. To a stirred solution of 4-acetylbenzoic acid (0.164 g, 1 mmol) and N-methyl-j?-anisidine (0.165 g, 1.2 mmol) in dry DCM (5 mL) and NEt3 (0.17 mL) was added DMAP (catalytic) and the solution was cooled on ice. To this was then added EDCI (0.383 g, 2 mmol) and the reaction was allowed to warm to rt with stirring over 22 h. To this was added sat. aq. bicarb, and DCM and the organic layer was separated and concentrated under reduced pressure. Purification by flash chromatography using an elution gradient of hexane to 30percent EtOAc in hexane gave the title compound, 0.186 g5 66 percent: 1H NMR delta (400 MHz, CDCl3) 2.47 (3H5 s), 3.40 (3H, s), 3.66 (3H5 s), 6.67 (2H5 d, J= 8.6 Hz), 6.89 (2H, d, J= 8.2 Hz)5 7.31 (2H, d5 J= 7.8 Hz)5 7.69 (2H5 d5 J= 7.8 Hz); 13C NMR delta (100 MHz, CDCl3) 26.5, 38.2, 55.2, 114.3, 127.5, 127.9, 128.5, 136.9, 137.0, 140.4, 158.0, 169.5, 197.4; LC/MS (APCI) m/z 304.47 (M-H)-; HPLC tT = 3.61 min (>99percent) 90percent MeCN m H2O.

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 5961-59-1.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
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Application of 437-83-2, 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 437-83-2 as follows.

Compound 123: 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-3-methoxybenzoic acid; [0590] 4-Bromo-3-fluoro-2-methoxyaniline: To 3-fluoro-2-methoxyaniline (2.8 g, 20 mmol) in 10 mL of acetic acid was added bromine (0.82 mL, 16 mmol) in acetic acid (10 rnL) dropwise. The reaction mixture was stirred at rt. for 30 min. Solid was filtered and washed with acetic acid to give the HBr salt. It was then dissolved in water, basified by addition of KOH, extracted with ethyl acetate. The organic layer was dried and concentrated to give a white solid (2.8 g, 80 %). 1U NMR (400 MHz, CHLOROFORM-J) delta ppm 3.93 (s, 3 H) 6.42 (dd, J=S.6, 1.8 Hz, 1 H) 7.01 (dd, J=8.6, 7.1 Hz, 1 H). [M+H] calc’d for C7H7BrFNO, 222; found 222.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/42711; (2009); A1;,
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