Ethers-buliding-blocks

Electric Literature of 29578-83-4, These common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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.

To a vigorously stirred mixture of 1 -Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMn04 (3.14g, 19.89 mmol) at 105C. The mixture which turned to a black suspension was stirred 24 hours at 105C, then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCI. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24% yield) as a white solid. MS: 229.1 [M+H]+, Rt (1 ) = 1 .18 min.

Statistics shows that 1-Bromo-3-methoxy-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 29578-83-4.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

The Pd-catalyzed cross-coupling reaction of 5-Bromo-l,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl~l,3-dimethoxybenzene 1 in excellent yield; Example 20 Synthesis of 5-AUyl-l,3-dimethoxybenzene5-Bromo-l,3-dimethoxybenzene (2.13 g, 9.8 mralphaol), CsF (2.88 g, 19.0 mmol), and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were weighed into a flame-dried Schlenk flask and put under a flow of argon. THF (80 mL) was added to the flask via syringe, and the resulting suspension was stirred for 30 min at room temperature. AHyI boronic acid pinacol ester (2.96 g, 17.6 mmol) in THF (40 ml) was added and the resulting mixture was heated to reflux for 30 h. Another portion of CsF (2.88 g, 19.0 mmol) and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were added and the reaction was continued to reflux for 24 h. The reaction mixture was diluted with petroleum ether (100 ml) followed by H2O (100 ml). The layers were separated and the aqueous layer was extracted with petroleum ether (2 x 80 ml). The combined organic layers were washed with H2O (100 ml), and brine (100 ml). The solution was dried over MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (silica, eluent: hexanes/benzene = 3:2) to give 1.60 g (92%) of 5-Allyl-l,3- dimethoxybenzene. 1H NMR (CDCl3): delta 3.33 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.77 (s, 6H, OCHi), 5.02-5.11 (m, 2H5. CH2CH=CH2), 5.89-5.99 (m, 1Eta, CH2CH=CH2), 6.33-6.38 (m, 3H).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; RUTERGS UNIVERSITY; WO2007/8847; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 3616-56-6

1) 1H, 1’H-2, 3′-twoversus(dimethylamino)Acetaldehyde acetalAccording to the molar ratio of 1:1 to 3,Stir in acetic acid for 6 hours.Rearrangement to obtain an intermediate with a yield of 91%

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; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Liu Feige; Zhuang Shaoqing; (28 pag.)CN109942581; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-methoxyaniline

To a solution of 5-bromo-3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine from step 3 (258 mg, 0.56 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (165 mg, 1.68 mmol), bis(pinacolato) diboron (569 mg, 2.24 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 130 C. for 3.5 hours. To this solution was added 3-bromo-5-methoxyaniline (113 mg, 0.56 mmol), potassium carbonate (232 mg, 1.68 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over magnesium sulfate. The mixture was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide 3-(3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methoxyaniline (154 mg, 55% yield): MS (ES) m/z 503 (M+H).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; Springer, John Robert; Hockerman, Susan L.; Anderson, David Randolph; (120 pag.)US2018/208594; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 17061-62-0, A common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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.

To a solution of bis(4-methoxybenzyl)amine 30.1 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq), followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer was extracted with DCM (2x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10- 80% EtOAc in hexanes) to provide the title compound 30.0 (1125 g, 3.22 mol, 92%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta 7.23 (dd, J = 2.08, 6.62 Hz, 4H), 6.90 (dd, J = 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (m, 6H), 2.92 (q, J = 7.40 Hz, 2H), 1.33 (t, J = 7.40 Hz, 3H). GC-LCMS (ESI pos. ion) m/z: = 372.2 (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:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 4179-19-5,Some common heterocyclic compound, 4179-19-5, name is 3,5-Dimethoxytoluene, molecular formula is C9H12O2, 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 3-necked round bottom flask was added 3,5-dimethoxytoluene (6.088g, 40mmol) and cyclohexane(28mL) under nitrogen.Was added dimethyl carbonate (30.3g,336mmol), at 60 deg.] Cand the reaction mixture was heated. After 15 minutes was added an excess of chlorosulfonic acid. By inserting the tubeof solid sodium hydroxide to remove HCl gas release. After the addition wascomplete, the reaction mixture was heated at 70-72 for one hour, then cooled toroom temperature. The solid was filtered off, washed with dimethyl carbonate /cyclohexane (1:1,20mL)and washed. The solid was dried under vacuum to give pure material (6.13g, 66%). To sulfonic acid (product fromthe above, 4.65g, 20mmol) and triethylamine(2.03g, 2.79mL) was added 2,4,6-trichloro-1,3,5triazine (cyanuric chloride, 3.69g, 20mmol)in (40 mL) in amixture of acetone-.The reaction mixture was heated at reflux for 20 hours, then cooled to room temperature. Thesolution was passed through a pad of Celite, and evaporated in vacuo to leave asolid, which was filtered off, washed with hexane. The product of cyanuric acidand hydroxides (cyanuric hydroxide) in a mixture of salt and triethylamine (was7.58 g) used in the next step without further purification. Fitted to acondenser (acetone – cooled with dry ice), 3-neck round bottom flask was addedthe mixture from step (was 7.58 g) and acetone (100mL). Thereaction mixture was cooled to -78 , ammonia gas intothe solution for 0.5hours. The reaction mixture was allowed to stand overnight, so that theammonia was slowlyevaporated, and then the solvent was evaporated. Water was added, the productwas extracted with DCM. The solvent was dried and evaporated to a mixture ofthe remaining solid and thick liquids. The solid was filtered off, washed withhexane, the remaining pure sulfonamide (3.23g,70%). To a round bottomflask was added 3,5-dimethyl-4-hydroxybenzoicacid (2.99g, 18mmol). Was added anhydrous DMF (20mL), and sodium hydride (1.8g, 45mmol). The reaction mixturewas stirred at roomtemperature for 1hour. Was added p-methoxybenzyl chloride (6.20g,39.6mmol), and the mixture was stirred at room temperature overnight (20 hours). Thereaction mixture was poured into water, acidified with 1N HCl and stirred for 1hour. The precipitated solid was filtered off, washed with water and hexane togive the pure B- cyclic structural unit (6.93g, 95%). The structural unitof the B- ring (6.93g, 17.1mmol) was dissolvedin a mixture of methanol(50mL) and tetrahydrofuran(50 mL) of. Waterwas added (20 mL) of potassium hydroxide (1.25g,22.2mmol). At 70 deg.] Cand the reaction mixture was refluxed for 24 hours. The solvent was evaporated in vacuo.Water was added, the reaction mixture was acidified with 1N HCl (pH4-5). Thesolid was filtered off, washed with water and hexanes. The yield was 4.61g (94%). Under nitrogen,above product (1.932g, 6.75mmol), and sulfonamidefrom above (1.04g, 4.5mmol) was added to a 3-neck round bottom flask. Dichloromethane was addedunder stirring (100mL). To this stirred mixture was addedN-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCI.HCl, 1.36g, 7.09mmol), followed by addition of N, N- dimethylaminopyridine(2.06g, 16.9mmol). At roomtemperature the reaction mixture was stirred for 24 hours, then washed with 1N HCI, 2.5%NaOH and saturated sodium bicarbonate solution. The organic layer was dried andevaporated in vacuo to leave a residue, which was purified by silica gel (100g)column chromatography using 20-50% hexane in ethyl acetate in methylenechloride and methanol as the eluting 5% purification agent. Fractions 30-66afforded pure material (1.35g, 60%). Under nitrogen,compounds from the previous step(0.105g, 0.21mmol) was dissolved in tetrahydrofuran, cooled to -78 . N-butyllithium was added, and the reaction mixture wasslowly warmed to roomtemperature and stirredovernight (~ 14 hours).TLC showed incomplete conversion. The reaction mixture was quenched withsaturated ammonium chloride solution, extracted with ethyl acetate. The solventwas evaporated in vacuo, the remaining residue, which was purified by silicagel (15g) column chromatography adopt in 20-50% ethyl acetate in hexanes aseluent. Product was not pure enough, thus making use of another pillar, the useof hexane in 0.5% methanol as eluent. Finally, the material was purified bypreparative TLC. Under nitrogen compounds from the previous step(0.277 g of) was dissolved in trifluoroacetic acid (10mL), and the reaction mixture was refluxed (bath temperature 80 ) 4 days. The solvent wasevaporated in vacuo, the residue was dissolvedin 0.25N NaOH (20mL), and acidified with acetic acid. At this time, the solidhas precipitated. The solid was filtered off, washed with water, washed withhexane, and dried. 0.005g of pure substances isolated from the batch. 0.060gcompound isolated from another batch, which is not enough pure. The compoundwas further purified by preparative HPLC, to give pure 6,8-dimethoxy-3-(4-hydroxy-3,5-dimethylphenyl) -2H-1,2- benzothiazine 1,1-…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxytoluene, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 701-56-4

General procedure: Under an atmosphere of N2, KOt-Bu (2.2 mmol), dioxane (0.9 mL), DMSO (1.65 mmol), tertiary amine 1 (0.55 mmol), and aryl halide 2 (1.65 mmol) were successively added to a Schlenk reaction tube. The mixture was stirred vigorously at 80-120 C for 12 h. Then the mixture was diluted with EtOAc, washed with sat. brine, and dried (anhyd Na2SO4). Then the solvent was removed under reduced pressure andthe residue was purified by flash column chromatography (petroleum ether and petroleum ether-EtOAc, 100:1 for the methoxy group derived products) to give pure products 3.

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; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 111-95-5, These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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.

The [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carbaldehyde (100 mg, 0.245 mmol) obtained in Example 47, bis(2-methoxyethyl)amine (70 mg, 0.53 mmol) and acetic acid (0.029 ml, 0.51 mmol) were dissolved in 1,2-dichloroethane (5 ml). To the resulting solution was added sodium triacetoxyborohydride (115 mg, 0.515 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 days. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The resulting mixture was separated into layers. The organic layer thus obtained was washed sequentially with a satu-rated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to afford a white solid. The resulting solid was washed with hexane to give the title compound (101 mg, 0.192 mmol, 78%) as a white powder. 1H-NMR(400MHz,CDCl3) delta: 2.73(4H,t,J=5.8Hz), 3.31(6H,s), 3.47(4H,d,J=5.8Hz), 3.75(2H,s), 5.93(1H,s); 6.88-6.97(1H,m), 6.97-7.07(1H,m), 7.38(2H,d,J=8.8Hz), 7.50-7.60(3H,m), 7.76(1H,dd,J=8.1,2.0Hz), 7.98-8.08(1H,m), 8.54(1H,d,J=2.0Hz). MSm/z: 525(M++H).

Statistics shows that Bis(2-methoxyethyl)amine is playing an increasingly important role. we look forward to future research findings about 111-95-5.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1640366; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Application In Synthesis of 1,3-Dibromo-5-methoxybenzene

2 mmol 3,5-dibromoanisole were dissolved in 10 ml THF and cooled to -78C. 2.4 mmol of n- BuLi were added dropwise and stirring was continued for 15 min. 3 mmol of methyl iodide were added and the mixture was allowed to slowly warm to ca. -200C over a period of ca. 2 h. IM HCl and dichloromethane were added and the phases were separated. 1.65 mmol of crude 3-bromo-5- methylanisole were taken to the next step without further purification.

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; KARO BIO AB; WO2008/43567; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 393-15-7 as follows. Recommanded Product: 393-15-7

Benzoic acid Z-17a (1.1 g, 3.0 mmol) is suspended in thionyl chloride and stirred for 1 h at 60 C. The reaction mixture is evaporated down and dried azeotropically with dry toluene. The acid chloride Z-18a (400 mg, 1.04 mmol) is then taken up in a little NMP (1.2 mL) and combined with 4-methoxy-3-trifluoromethyl-phenylamine E-2a (188 mg, 1.55 mmol) and DIPEA (300 muL, 1.75 mmol). For working up water is added, the precipitate obtained is filtered off, dried and Example compound III-2 (HPLC-MS: tRet.=2.20 min; MS (M+H)+=540) is obtained.

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/94975; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem