Category: ethers-buliding-blocks

Electric Literature of 1836-62-0, A common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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.

General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3).

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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. Application In Synthesis of O-(2,4-Dimethoxybenzyl)hydroxylamine

General procedure: To a solution of 2a (0.200 g, 0.651 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl, 0.150 g, 0.781 mmol)and 4-dimethylaminopyridine (DMAP, 8 mg, 0.065 mmol) in CH2Cl2(30 mL) was added O-benzylhydroxylamine hydrochloride (0.125 g;0.781 mmol) and N-methylmorpholine (NMM, 0.086 mL, 0.781 mmol),and the mixture was stirred at room temperature (r.t.) for 16 h. Thefinal solution was evaporated, dissolved in EtOAc (25 mL) and washedwith 0.1 M HCl (3 ¡Á 25mL), 0.1 M NaOH (2 ¡Á 25 mL) and then H2O(1 ¡Á 25 mL). The final organic phase was dried over anhydrous Na2SO4,and the solvent evaporated. The crude was recrystallized from Et2O/n-hexane, affording the pure compound as white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 216067-66-2, its application will become more common.

Reference:
Article; Marques, Sergio M.; Abate, Claudia C.; Chaves, Silvia; Marques, Fernanda; Santos, Isabel; Nuti, Elisa; Rossello, Armando; Santos, M. Amelia; Journal of Inorganic Biochemistry; vol. 127; (2013); p. 188 – 202;,
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Synthetic Route of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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 lithium 3-[(2-Dimethylamino-ethyl)-methyl-amino]-lH-indazole- 6-carboxylate (77mg, 0.29 mmol) in anhydrous DMF (5mL) was added EDC (140mg, 0.73mmol) and etaOBt (47mg, 0.35mmol). The mixture was stirred for 10 min. then Et3N (0.16mL, 0.1.16mmol) and 4-trifluoromethoxybenzylamine (0.049mL, 0.32 mmol) were added. The mixture was heated at 50 0C for 15 hr. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (25 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography on silica yielded the title compound (37mg, 29%). m/z (M+eta) = 436.45.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-(Trifluoromethoxy)phenyl)methanamine, its application will become more common.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61109; (2008); A2;,
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321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 3-fluoro-4-methoxybromobenzene Into a flask of 5 l were charged 384 g (3.04 mol) of 2-fluoroanisole and 2.5 l of chloroform, to which was added dropwise 504 g (3.16 mol) of bromine over about 3 hours while cooling on an ice water bath at 10 C. The resulting mixture was stirred at room temperature over a night and heated under reflux for 8 hours. After the air cooling, the product was added with 1 l of water and 50 g of sodium bisulfite and sufficiently shaken to separate into two layers. The resulting organic layer was washed with an aqueous solution of 5% sodium hydrogen carbonate and further with 1 l of water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and distilled under a reduced pressure (4 mmHg, bp: 93-96 C.) to obtain 585 g (yield: 94%) of 3-fluoro-4-methoxybromobenzene.

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

Reference:
Patent; Nippon Mining Co., Ltd.; US5098602; (1992); A;,
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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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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. 59557-91-4

(0900) Under the protection of nitrogen gas, 4-bromo-2-methoxyaniline (15 g, 74.24 mmol) was dissolved in 1,4-dioxane (250 mL), and a solution of sodium bicarbonate (15.8 g, 188.07 mmol) in water (150 mL) was added. At 0 C., carbobenzoxy chloride (19.1 g, 111.96 mmol) was added dropwisely to the reaction system. After the addition, the reaction was carried out at room temperature for 20 min. TLC detection showed that raw materials disappeared. The mixture was extracted with ethyl acetate (100 mL¡Á3). The organic phases were combined, washed with saturated saline solution (100 mL¡Á2), dried with anhydrous sodium sulfate, and concentrated in vacuum. The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:5) to get the title compound as a white solid (15 g, yield: 60%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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60789-54-0, Adding a certain compound to certain chemical reactions, such as: 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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 60789-54-0.

3-Benzyloxybutyl-cyclopent-2-enone A solution of a Grignard reagent was prepared following the procedure described in the synthesis of 3-(5-hexenyl)cyclopent-2-enone, using Mg turnings (302 mg, 12 mmol), THF (11 mL), and benzyl 4-bromobutylether (2.75 g, 11.3 mmol).

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-Bromobutoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Massachusetts Institute of Technology; US6465664; (2002); B1;,
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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. 450-91-9, name is 4-Fluoro-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 450-91-9

Step 1: 2-bromo-4-fluoro-6-methoxyaniline To a solution of 4-fluoro-2-methoxyaniline (14.4 g, 0.1 mol) in 300 mL of dry DMF was added NBS (17.8 g, 0.1 mol) in small portions at 0-5¡ã C. under nitrogen, then the resulting mixture was stirred at room temperature overnight. The mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-bromo-4-fluoro-6-methoxyaniline (28 g crude).

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arrington, Kenneth L.; Burgey, Christopher; Gilfillan, Robert; Han, Yongxin; Patel, Mehul; Li, Chun Sing; Li, Yaozong; Luo, Yunfu; Lei, Zhiyu; US2014/100231; (2014); A1;,
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Adding some certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7. 5414-19-7

To a room temperature mixture of the [T-BUTYL-2- ( {4- [4- (2-] ethoxyethoxy) phenyl] phenyl) sulfonyl) acetate product (4) from Part C (800 mg, 1.9 mmol) in 8 mL DMF was added 18-crown-6 (150 mg, 0.6 mmol), potassium carbonate (1.3 g, 9.5 mmol), and bis (2-bromoethyl) ether (480 mg, 2.1 mmol). The mixture was stirred at room temperature for 18 hr. Subsequently, no starting material (4) was detectable by HPLC. The resulting mixture was concentrated, diluted in cold ether, and filtered to produce 800 mg (86% yield) of the desired compound (5). LCMS: [[M+NA] =] 513.2.

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 1-Bromo-2-(2-bromoethoxy)ethane.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
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41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

In a 25 mL single neck flask, the intermediate 4 (0.4 g, 1.21 mmol), (3- methoxyphenyl)-N-methylmethanamine (1.09 g, 7.23 mmol), Cul (0.023 g, 0.12 mmol) and l-methylpyrrolidin-2-one (3 mL) were added and the resulting mixture was heated at 150 0 C for 12 h and worked up. The reaction mixture was partitioned in dichloromethane/water and the organic layer was separated. The organic phase was dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to obtain the pure 7-(N-(3-methoxybenzyl)-N-methylamino)-l-benzyl-6-fluoro-l, 4-dihydro-4- oxoquinoline – 3-carboxylic acid (25 mg); Yield: 4.63%; H NMR (400 MHz, CDCb): delta 15.0 (s, IH), 8.77 (s, IH), 8.01 (d, J=14, IH), 7.33 (s, 3H), 7.22-7.26 (t, IH), 7.04 (d, J=18.4, 2H), 6.82 (d, J=7.2, IH), 6.70-6.74 (m, 2H), 6.52 (d, J=5.6, IH), 5.30 (s, 2H), 4.43 (s, 2H), 3.71- 7.76 (m, 3H), 2.92(s, 3H); MS(ESI): 447.0(M+H); HPLC: 98.0%.

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 41789-95-1.

Reference:
Patent; NIROGYONE THERAPEUTICS, INC.; SANDANAYAKA, Vincent; WU, Qiong; (80 pag.)WO2016/81464; (2016); A1;,
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Some common heterocyclic compound, 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, molecular formula is C8H10FNO, 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. 123652-95-9

Compound 33; To a solution of compound 32 (0.185 mmol, 100 mg, 1.0 equiv.) in NMP (2 ml) was added 3- fluoro-4-methoxybenzylamine (1.850 mmol, 287 mg, 10 equiv.). The reaction mixture was heated to 100 0C and stirred overnight. Mixture was then poured into H2O and extracted withEtOAc. The combined organic layers were washed with water and brine, dried (Na2SC>4), filtered and concentrated in vacuo. 70 mg of compound 33 was obtained in 62% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123652-95-9, its application will become more common.

Reference:
Patent; N.V. ORGANON; PHARMACOPEIA INC.; WO2008/51826; (2008); A2;,
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