Ethers-buliding-blocks

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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 1535-75-7

To a solution of 2-(trifluoromethoxy)aniline (318A) (2.655 mg, 15 mmol) in acetic acid (6 mL) was added NBS (2.94 g, 16.5 mmol) at 0 C and stirred at room temperature overnight. It was concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to afford Compound 318B. LC-MS (ESI) m/z: 256 [M +H]+; ‘H-NMR (CDCb, 400 MHz): d (ppm) 3.89 (s, 2H), 6.67 (d, J= 8.8 Hz, 1H), 7.18 (dd, J= 8.8, 2.4 Hz, 1H), 7.28 (d, J= 2.4 Hz, 1H).

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Ether – Wikipedia,
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111-95-5, 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. 111-95-5 name is Bis(2-methoxyethyl)amine, 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.

General procedure: An oven-dried 20 mL pressurevial was charged with monoester No.13a-f (1.0 eq) and dissolved in anhydrous DMF (0.5 mL/0.1mmol of the monoester). The corresponding amine (1.2 eq) was added, followed by HBTU (1.0 eq).The resulting solution was stirred at 0 C for 5 min, then TEA (2.0 eq) was added and stirring at 0 Cwas continued for 0.5 h. The resulting mixture was warmed to room temperature and stirring wascontinued for 2 h. The brownish solution was diluted with water (20 mL) and extracted with EtOAc(3 x 15 mL). Combined organic extracts were washed with water (15 mL), brine (15 mL), dried overanhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(2-methoxyethyl)amine, and friends who are interested can also refer to it.

Reference:
Article; Zogota, Rimants; Kinena, Linda; Withers-Martinez, Chrislaine; Blackman, Michael J.; Bobrovs, Raitis; Pantelejevs, Teodors; Kanepe-Lapsa, Iveta; Ozola, Vita; Jaudzems, Kristaps; Suna, Edgars; Jirgensons, Aigars; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 344 – 352;,
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Ether | (C2H5)2O – PubChem

398-62-9, name is 4-Fluoro-1,2-dimethoxybenzene, 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. 398-62-9

EXAMPLE 138 6-Bromo-1-(2-fluoro-4,5-dimethoxyphenyl)-1-hexanone A solution of 5.3 g (0.034 mol) of 1,2-dimethoxy-4-fluorobenzene in 25 mL of methylene chloride was added to a solution of 5.4 g (0.041 mol) of aluminum chloride and 8.7 g (0.041 mol) of 6-bromohexanoyl chloride in 60 mL of methylene chloride cooled in an ice bath. The resulting solution was kept at 0 for 5 hours and then worked up as in Example 131. The crude product was recrystallized from methylene chloride-ether to give 6.98 g (62% yield), mp 81-83, of 6-bromo-1-(2-fluoro-4,5-dimethoxyphenyl)-1-hexanone. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 332 (C14 H18 BrFO3).

Statistics shows that 398-62-9 is playing an increasingly important role. we look forward to future research findings about 4-Fluoro-1,2-dimethoxybenzene.

Reference:
Patent; Hoffmann-La Roche Inc.; US5025036; (1991); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 456-49-5, name is 1-Fluoro-3-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 456-49-5, 456-49-5

EXAMPLE 3 A solution of butyllithium in hexanes (2.5 M; 15.9 ml) was added to a stirring solution of 3-fluoroanisole (5.0 g) in dry tetrahydrofuran (100 ml) at -78 C. and the mixture stirred at that temperature for 30 min. Dry dimethylformamide (3.1 ml) was added and the mixture stirred and allowed to warm to ambient temperature during one hour. Water (150 ml) was added and the mixture extracted with ethyl acetate (3*100 ml). The combined extracts were washed with brine (100 ml), dried over magnesium sulphate, and the solvent removed in vacuo. Distillation of the residue under reduced pressure gave 2-fluoro-6-methoxybenzaldehyde (4.6 g) as an oil b.p. 120 C. at 10.66 mbar.

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-Fluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Knoll Aktiengesellschaft; US5935973; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

24332-20-5, The chemical industry reduces the impact on the environment during synthesis 24332-20-5, name is 1,1,2-Trimethoxyethane, I believe this compound will play a more active role in future production and life.

Example 10 A flask was charged with methoxyacetaldehyde dimethylacetal (1.2 equiv.), trifiuoroacetic acid (1.3 equiv.), and water (equal volume to TFA), and the mixture was stirred at 50 C for 10 min. The reaction mixture was then removed from the heating bath and TEA (1.3 equiv.) was added followed by a solution of 3-(N-Boc-aminomethyl)-azetidine (1 equiv.) in EtOH and DCM, and then NaBH(OAc)3 (3 equiv.). The reaction was stirred for 12 hrs at 20 C. The reaction mixture was extracted and distilled to remove some ethanol. To the organic layer was added 5M HC1 in iPrOH (7 equiv.) at 50 C. TBME was added at 48 C over 45 min, and cooled to 20 C over 60 min. The reaction stirred for another 60 min, filtered, and the filter cake was washed with TBME. The organic layer was dried to provide l-(2-methoxyethyl)-3- (methylamino)-azetidine dihydrochloride.

The chemical industry reduces the impact on the environment during synthesis 1,1,2-Trimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SATORI PHARMACEUTICALS, INC.; BRONK, Brian, Scott; AUSTIN, Wesley, Francis; CREASER, Steffen, Phillip; FULLER, Nathan, Oliver; HUBBS, Jed, Lee; IVES, Jeffrey, Lee; SHEN, Ruichao; WO2013/36669; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9, The chemical industry reduces the impact on the environment during synthesis 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, I believe this compound will play a more active role in future production and life.

step Bl – Ethyl phenylcyanoacetate (22, 18.3 mL, 0.1054 mol, Ar1 = Ph) was added dropwise to a suspension of NaH (4.85 g, 0.1213 mol, 60percent dispersion in oil) in DMF (200 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 30 min then benzyl 2-bromoethyl ether (20 mL, 0.1265 mmol) was added. The reaction mixture was then stirred at 60 C overnight, cooled to RT and partitioned between EtOAc and a saturated aqueous NH4Cl. The aqueous layer was thrice back- extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by Si?2 chromatography eluting with a EtOAc/hexane gradient (5 to 95percent EtOAc) to afford 20 g (60percent) of 24a.

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

b) 3-[2-(2,4-dimethoxybenzylamino)pyridin-4-yl]-/V-(1-methylpiperidin-4- yl)imidazo[1,2-b]pyridazin-6-amineTo a solution of 3-(2-chloropyridin-4-yl)-//-(1-methylpiperidin-4-yl)imidazo[1 ,2-b]pyridazin-6- amine (100 mg, 0.29 mmol) and NaO’Bu (39 mg, 0.41 mmol) in DME (2 mL) was added a pre-mixed solution of Pd(OAc)2 (3 mg, 0.015 mmol) and CyPF-‘Bu (8 mg, 0.015 mmol) in DME (1 mL). The reaction mixture was stirred for 5 min before 2,4-dimethoxybenzylamine (68 mg, 0.41 mmol) was added and the mixture heated at 100C for 18 h. The reaction mixture was concentrated in vacuo and purification by column chromatography (EtOAc-2M NH3 in MeOH gradient) gave an off-white solid (77 mg, 56%); 1H NMR (400 MHz, CD3OD) delta ppm 7.94 (d, J=6.0 Hz, 1H), 7.85 (s, 1 H), 7.62 (d, =9.6 Hz, 1 H), 7.51 (s, 1 H), 7.24 (dd, J=5.7, 1.6 Hz, 1H), 7.21 (d, J=8.2 Hz, 1 H), 6.72 (d, J=9.6 Hz, 1 H), 6.54 (d, J=2.3 Hz, 1 H), 6.46 (dd, J=8.2, 2.3 Hz, 1H), 4.43 (s, 2H), 3.83 (s, 3H), 3.82-3.76 (m, 1H), 3.75 (s, 3H), 2.88-2.77 (m, 2H), 2.23-2.09 (m, 7H), 1.68-1.53 (m, 2H); m/z (ES+APCI)+: 474 [M+H]+.

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, 20781-20-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5.

General procedure: A mixture of aryl halide (0.25 mmol), phenylboronicacid (0.3 mmol), Na2CO3 (0.25 mmol), PPh3 (0.025 mmol)and Pd(at)PAAs-CD (0.5 mg, 0.2 mol% Pd per mol of arylhalide) were placed into a 10 mL Schlenck tube with1 mL H2O. The reaction mixture was reacted at 80 C for18 h, and the reaction progress was monitored via gaschromatography mass spectrometry (GC-MS). The reactionmixture was allowed to cool to room temperature, andthen 3 mL water was added, and the product was extractedwith ethyl acetate (3 mL ¡Á 3). The organic layers werecombined and dried over anhydrous Na2SO4 and solventswere evaporated via rotary evaporator. The crude productwas purified by column chromatography (200-300 meshsilica) using a mixture of petroleum ether/ethyl acetate(10:1, v:v) as eluent. The structures of the products wereconfirmed by 1H NMR and 13C NMR spectroscopies.

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wei; Yao, Zi-Jian; Deng, Wei; Journal of the Brazilian Chemical Society; vol. 30; 8; (2019); p. 1667 – 1677;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 6346-09-4

Amine 1 (Aldrich) (3. 5g, 21.7 mol) was dissolved in a mixture of chloroform (30 ml) and IN sodium hydroxide (24 ml) and [15ML] of mesitylenesulfonyl chloride dissolved in [1 SML] of chloroform were added at [5C.] The mixture was stirred for 2h, the reaction mixture was then diluted with chloroform (50 ml), the organic layer was separated, washed with a saturated solution of ammonium chloride, dried [(NA2S04),] and evaporated to dryness. The residual oil crystallized after drying and was used in the next step without further purification; 7. 0g (95%) of 2 were obtained [;’HNMR (CDC13)] : [PPM] 1.15 (t, 6H), 1.55 (m, 4H), 2.30 (s, 3H), 2.65 (s, 6H), 2.95 (q, 2H), 3.40-3. 55 [(M,] 4H), 4.40 (t, 1H), 4.90 (t, 1H), 6.95 (s, 2H) [; 13CNMR (CDCL3)] : [PPM] 15.19, 20.80, 22.85, 24.55, 30.83, 42.39, 61.40, 102.41, 131.84, 133.82, 138.99, 141.92.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLIL BIOMEDICAL CORPORATION; WO2004/2991; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

398-62-9, A common heterocyclic compound, 398-62-9, name is 4-Fluoro-1,2-dimethoxybenzene, molecular formula is C8H9FO2, 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 suspension of sulfur trioxide N,N-dimethylformamide complex (4.108 g, 27 mmol) in 1,2-dichloroethane was added 4-fluoroveratrole (3.49 g, 22 mmol) dropwise. The mixture was slowly heated to 85 C. in an oil bath. After 2.5 h, the solids had dissolved to afford a golden yellow solution. A trace of starting material was still present and heating was continued for a further 4.5 h. The oil bath was removed and thionyl chloride (1.95 ml, 27 mmol) added dropwise. The mixture was heated 4 h at 85 C. and allowed to cool to room temperature. The solution was poured into water and extracted with dichloromethane (3¡Á50 ml), the combined organics washed with water, dried over magnesium sulfate and evaporated. Remaining traces of N,N-dimethylformamide were removed azeotropically with toluene to afford the product as an off-white solid that was used without further purification. EI MS: m/e=254.0 ([M]+).

The synthetic route of 398-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Plancher, Jean-Marc; Taylor, Sven; US2005/165012; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem