Ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 458-03-7, name is 1-Ethoxy-3-fluorobenzene, 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 458-03-7, 458-03-7

First Step In a reaction vessel under a nitrogen atmosphere, 1.94 g (7.2 mmol) of 2-(4-ethoxy-2-fluoro-3-trimethylsilylphenyl)acetate (No. 5) obtained in the fourth step in Example 1 was dissolved into 25 mL of THF. The solution was cooled to 0 C., 8.6 mL (14.4 mmol) of s-butyllithium (1.67 M n-hexane solution) was added dropwise thereto, and subsequently the reaction mixture was heated to room temperature and stirred for 30 minutes. Subsequently, the resultant reaction mixture was cooled to -70 C., a THF (15 mL) solution of 1.9 g (7.2 mmol) of 2-(trans-4-propyl-cyclohexyl)cyclohexyl-oxetane (No. 26) obtained according to a method described in JP 2000-8040 A, and subsequently a THF (3 mL) solution of 1.08 mL (8.6 mmol) of boron trifluoride-diethyl ether complex were added dropwise thereto.

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-Ethoxy-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; Goto, Mayumi; Fujimori, Sayaka; US9102871; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

702-24-9, 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. 702-24-9 name is 4-Methoxy-N-methylbenzylamine, 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.

3-( 5-amino-4-fluoro-2-methylphenyl)-7 -chloro-1-methyl-1 ,6-naphthyridin-2(1H)one(1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol,1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) andheated at 180¡ãC under Ar overnight. The mixture was cooled to R T and poured onto H20(200 mL). The resulting solids were collected by filtration, rinsed very well with H20, driedon the filter to dampness and then dissolved in EtOAc. The solution was dried (MgS04),filtered and evaporated to afford 7-(( 4-methoxybenzyl)(methyl)amino )-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittlebrown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): 88.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 8.8 Hz, 2H), 6.86-6.82 (m,1H), 6.57 (d, J = 9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s,3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H(

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

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

101-55-3, Adding some certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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 101-55-3.

General procedure: Reactions were conducted using standard dry box techniques and all solvents were distilled over Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.Reactions were conducted using standard dry box techniques and all solvents were distilled oversodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was thenpurified by column chromatography on silica gel.sodium. Method A: To a screw capped vial was added Pd(dba)2 (0.010 mmol), DTBNpP(0.020mmol), and NaH (1.2 mmol). The vial was sealed with a septa screw cap and removedfrom the glove box. To the vial was added toluene (1.0 mL), aryl bromide (1.0 mmol), anddiethyl malonate (1.2 mmol). The reaction mixture was stirred at 70 C for 24 hours and theconversion of the aryl bromide was then measured by GC. The crude reaction mixture wasfiltered through a plug of Celite and then concentrated in vacuo. The concentrate was then purified by column chromatography on silica gel.

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 101-55-3.

Reference:
Article; Semmes, Jeffrey G.; Bevans, Stephanie L.; Mullins, C. Haddon; Shaughnessy, Kevin H.; Tetrahedron Letters; vol. 56; 23; (2015); p. 3447 – 3450;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

22094-18-4, 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of NaH (4.08 g, 102 mmol) (60% in oil) in DMF (50 mL) was added a solution of 2-(4-bromophenyl)acetonitrile (10 g, 51 mmol) in DMF (50 mL) dropwise at 0 C, followed by the addition of 1,3 -dibromo-2,2-dimethoxy propane (13.4 g, 51.0 mmol) at 0 C. The mixture was stirred at 60 C for 18 h. After cooling to RT, the reaction was quenched by adding water (250 mL) and extracted with EtOAc (150 mLx3). The organic layers were combined, washed with brine, dried over Na2SC>4, filtered and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (PE : ethyl acetate =40: 1 to 30: 1) to give the title compound. MS (EI) m/z 296 [M+H]+.

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., 22094-18-4

To a solution of 2-(2,5-difluoro-4-methylphenyl)acetonitrile (16.7 g, 100 mmol) in DMSO (200 mL) was added NaH (8 g, 200 mmol, 60% oil dispersion), portion-wise, at RT. The reaction was stirred for 1 h at RT, and then l,3-dibromo-2,2-dimethoxypropane (39.3 g, 150 mmol) was added. The mixture was heated at 60 C for 6 h. The reaction was quenched with water (100 mL) at 0 C and extracted with EtOAc (2 x 100 mL). The organic extracts were combined and washed with brine (2 x 50 mL), dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleumn ether/EtOAc (4/1) as eluting solvents to afford the title compound as a yellow solid (12 g, 45% yield). lU NMR(400 MHz, DMSO- ) delta 7.36-7.28(m, 2H), 3.18(s, 3H), 3.05(s, 3H), 3.03 (d, / = 13.6 Hz, 2H), 2.77 (d, / = 13.6 Hz, 2H), 2.24 (d, / = 1.6 Hz, 3H). LCMS (ESI): m/z = 268.0 [M+H]+.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; GANCIA, Emanuela; LADDUWAHETTY, Tammy; VESEY, David; WINSHIP, Paul; RENE, Olivier; (168 pag.)WO2017/5900; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, 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.

c) 2-Hvdroxyimino-Lambda/-(4-methoxy-3-methylphenyl)acetamideChloral hydrate (11.5 g, 70 mmol) and anhydrous sodium sulfate (60 g, 422 mmol) were added to vigorously stirred water (300 ml_). A slurry prepared by mixing hydroxylamine5 hydrochloride (23.0 g, 331 mmol) and 4-methoxy-3-methylphenylamine (10.0 g, 73 mmol) with aqueous hydrochloric acid (2.4 M, 250 ml.) was added to the above mixture. The resulting mixture was refluxed for 20 min and then allowed to stand at room temperature for 16 h. A precipitate formed and was collected by filtration. The solid was washed with water and dried to yield 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide (6.7 g,10 32 mmol, 44%)Data for 2-hydroxyimino-N-(4-methoxy-3-methylphenyl)acetamide: MS (ESI) m/z: 209 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-3-methylphenylamine, its application will become more common.

Reference:
Patent; AKZO NOBEL N.V.; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/95014; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

446-59-3, A common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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: The 2-bromo-1-ethoxy-4-fluoro-benzene (0.1 mol) was dissolved in THF (25 ml). The solution was cooled to -75 C and a solution of n-BuLi (9.73 ml, 2.4 M in hexane) was added slowly. The mixture was stirred for 30 min at -75 C. Trimethylborate (0.1 mol) was added within 5 min. Acetic acid (0.1 mol) and a 30% solution of H2O2 (0.1 mol) were added sequentially. The mixture was stirred for 30 min at 0 C and for 3 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography to yield the objected compound.

The synthetic route of 446-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Heng; Xu, Xiangqing; Chen, Yin; Qiu, Yinli; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 524 – 539;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 126-38-5

To a mixture of 3-bromobenzenethiol (8.7 g, 46 mmol) and l -bromo-2,2- dimethoxypropane (8.4 g, 46 mmol) in NN-dimethylformamide (50 mL) was added potassium carbonate (9.5 g, 69 mmol) at room temperature. The mixture was stirred at 80 C overnight. On completion, the reaction mixture was quenched with water and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude compound B-287 (13 g, 97% yield) as a colorless oil.

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, 126-38-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The chemical industry reduces the impact on the environment during synthesis 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, I believe this compound will play a more active role in future production and life. 14869-41-1

To a suspension of compound 26-5 (0 1 g) and 2-chloroethoxy acetic acid (45 4 mg) m DMF (2 mL), was added4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholmium chloride (DMT-MM, 87 7 mg) The reaction mixture was stirred at room temperature overnight Then, according to the Step 29-1 in synthetic method for EXAMPLE 29, cychzation reaction was pursued to obtain compound 30-1 (90 mg) as a colorless amorphous solid

The chemical industry reduces the impact on the environment during synthesis 14869-41-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SCHERING CORPORATION; NISHIDA, Hidemitsu; SAITOH, Fumihiko; HIRABAYASHI, Tomokazu; CHACKALAMANNIL, Samuel; CHAN, Tin-Yau; CHELLIAH, Mariappan, V.; CLASBY, Martin, C.; DWYER, Michael, P.; GREENLEE, William, J.; XIA, Yan; WO2010/65717; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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. 1462-37-9

After flushing the interior of the vessel with nitrogen, under nitrogen, 8.41 g (210 mmol) of sodium hydride (oily) and 80 ml of dry tetrahydrofuran were added to a 1000 ml four-necked flask, and while cooling with an ice-water bath, 34.00 g (100 mmol) in 350 ml of tetrahydrofuran was added dropwise. Immediately after the dropwise addition of DCMI in tetrahydrofuran solution, bubbles that appeared to be H 2 were observed. After foaming subsided, the temperature was raised to room temperature and stirred for 1 hour. Thereafter, while cooling the flask again with an ice-water bath, a solution of 50.01 g (233 mmol) of benzyl-2-bromoethyl ether dissolved in 50 ml of dry THF was added dropwise. After the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes, then heated to 60 to 70 ¡ã C. and stirred for 18 hours. On the way, heating was stopped when benzyl-2-bromoethyl ether became a trace amount and consumption ceased almost at a time-dependent change by TLC.As a post-treatment, the flask was cooled with ice with stirring under nitrogen, 150 ml of ethyl acetate was added to the flask, then 100 ml of water was slowly added dropwise, the aqueous phase was separated off and the organic phase was washed with 100 ml of water For 2 times. The organic phase was concentrated with an evaporator to obtain 68.10 g of a viscous liquid with a yellowish tinge. Thereafter, silica gel column purification was carried out using a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 10/1 to 1/1 (volume ratio)), and the solvent was distilled off under reduced pressure to give the following compound 6 46.36 g (76.2 mmol: yield 76.2percent) was obtained as a viscous liquid.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; Machine: Mitsubishi ChemicalsCo ., Ltd .; Imai Nao Akira; Saito Yasuyo; Kawakami Kotoku; Fuji Tsuu Akira; (94 pag.)JP2017/222625; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem