Category: ethers-buliding-blocks

Electric Literature of 349-65-5, The chemical industry reduces the impact on the environment during synthesis 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

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

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

Place ethyl 6,8-dichloroimidazo[ 1 ,2-bj pyridazine-3 -carboxylate (3 g, 11.54mmol), 1-(4-methoxyphenyl)-N-methylmethanamine (2.267 g, 15.00 mmol), and N,NDiisopropylethylamine (DIPEA) (4.03 mL, 23.07 mmol) in a 100 mL round bottle flask along with THF (15 mL). It was sealed and heated to 80°C for 6 hours. The reactionmixture was concentrated and purified with silica gel chromatography. The product came out when eluting with 35percent ethyl acetate in hexane. The fractions containing product was collected and concentrated to provide the product (3.7 g, 9.87 mmol, 86percent yield, 100percentpurity). LC retention time 1.06 mm [Al. MS (ES+) m/z: 375 (MH). ?H NMR (400MHz, CHLOROFORM-d):8.14 – 8.09 (m, 1H), 7.20 – 7.13 (m, 2H), 6.89 – 6.83 (m, 2H), 6.11 (s, 1H), 5.49 (s, 2H),4.44 (q, J=7.2 Hz, 2H), 3.84 – 3.77 (m, 3H), 3.17 (s, 3H), 1.42 (t, J=7.2 Hz, 3H)

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; DUNCIA, John V.; SPERGEL, Steven H.; (76 pag.)WO2018/93968; (2018); A1;,
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., Application In Synthesis of 4-Methoxy-N,N-dimethylaniline

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 and the 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

17061-62-0, name is Bis(4-methoxybenzyl)amine, 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. SDS of cas: 17061-62-0

To a stirred solution of 100.1 (100 g, 0.39 mol) in DCM (1 L) was added TEA (71 mL, 0.51 mol), followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.47 mol). The internal temperature was kept between 5-10 C during the addition of methane sulfonyl chloride. Once the addition was complete, the cooling bath was removed and the mixture was stirred at RT until TLC analysis indicated that the reaction was complete. Thereafter, water (1 L) was added, the layers were separated and the aqueous layer was extracted with DCM (2 x 500 mL). The combined organic layers were washed with brine (2 x 1 L), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column, employing a gradient of 10-80% EtOAc in hexanes, to afford 120 g (0.36 mol, 92%) of 101.0 as white solid.1H-NMR (400 MHz, CDCl3) delta 7.26 (dd, J=2.12, 6.60 Hz, 4H) 6.91 (dd, J=2.12, 6.62 Hz, 4H) 4.28 (s, 4H) 3.83 (s, 6H) 2.75 (s, 3H).

The synthetic route of 17061-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 60789-54-0, These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)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.

Reference Example 18 4-Benzyloxy-3-(4-benzyloxybutoxy)benzonitrile 4-Benzyloxy-3-hydroxybenzonitrile (3.4g) and potassium carbonate (6.3g) were dissolved in N,N-dimethylformamide (20mL). To the mixture was added benzyl 4-bromobutylether (3mL), and the mixture was stirred at 50C for 16 hours. To the reaction mixture was added dropwise 2mol/L hydrochloric acid (4mL), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent:ethyl acetate/hexane=1/5) to give the title compound (5.9g). 1H-NMR (CDCl3) delta ppm: 1.70-2.10 (4H, m), 3.55 (2H, t, J=6.1Hz), 4.04 (2H, t, J=6.5Hz), 4.49 (2H, s), 5.17 (2H, s), 6.90 (1H, d, J=8,2Hz), 7.08 (1H, d, J=1.9Hz), 7.19 (1H, dd, J=1.9Hz, 8.2Hz), 7.24-7.45 (10H, m)

Statistics shows that ((4-Bromobutoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 60789-54-0.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1698635; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Intermediate 14: step a 4-Bromo-2-isothiocyanato-1-methoxy-benzene A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

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; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
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. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of (2-Bromoethoxy)benzene

General procedure: Anhydrous K2CO3 (1.2 M equiv) was added to the solution of GA or compound 42 (0.2 mmol) and halogenating agents (1.2 M equiv) in dry DMF (5 mL). The reaction mixture was stirred at room temperature until the starting material was not observed by TLC. The mixture was treated with H2O (20 mL), the aqueous layer was extracted with EtOAc (2×20mL). The joined organic extracts were washed three times with H2O (60 mL) and saturated NaCl (60 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was chromatographed using a silica gel column to afford the pure target products.

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry Letters; vol. 22; 10; (2012); p. 3473 – 3479;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, 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 168268-00-6, name: 4-(Benzyloxy)-3-fluoroaniline

A solution of 1.23 L of acetone and 600 ml of water in sodium carbonate (132 g, 1.25 mol) was added to the oil and thenCool down to 05C, add benzyl chloroformate (127.8g, 0.748mol) dropwise, continue stirring for 15min,Filtration gave 133 g of a yellow solid as a compound of formula (4) with a yield of 98.9%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Zeng Huang; Zhang Zixue; Liu Yu; Pan Deng; Zou Lei; Zhang Yi; (8 pag.)CN108069919; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 36805-97-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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.

General procedure: To a Schlenk tube (20 mL) were added PdCl2(MeCN)2 (26 mg, 0.10 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.16 g, 0.40 mmol). The Schlenk tube was capped with a rubber septum and then evacuated and purged with argon. The evacuation-purge operation was repeated twice. To the tube was added 1,4-dioxane (6.0 mL), 1,2-dibromobenzene (1.63 g, 0.82 mL, 5.0 mmol), NEt3 (3.04 g, 4.18 mL, 30.0 mmol), and pinacolborane (2.18 mL, 1.92 g, 15.0 mmol) in this order with syringes, respectively, through the septum. The reaction mixture was heated at 110 C and the progress of the reaction was monitored by gas chromatography. After the complete consumption of the dibromide was confirmed, the reaction mixture was then allowed to cool to room temperature. The resulting solution was filtered through a thin pad of Celite with EtOAc as the eluent. The organic solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography on silica gel followed by recrystallization from hexane at -20 C, giving rise to 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (3h, 0.83 g, 51%) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Shimizu, Masaki; Nagao, Ikuhiro; Tomioka, Yosuke; Kadowaki, Tsugumi; Hiyama, Tamejiro; Tetrahedron; vol. 67; 41; (2011); p. 8014 – 8026;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem