Category: ethers-buliding-blocks

Reference of 171290-52-1, 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. 171290-52-1 name is 3,5-Dimethoxyphenylacetylene, 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: trans-1,2-dichloroethylene 7(2.0 equiv.), terminal acetylenes (1.0 mmol, 1.0 equiv.), PdCl2(PPh3)2 (2.0 mol%), CuI (4.0 mol%), piperidine (2.0 equiv.) and 4 mL diethyl ether were mixed together and stirred under nitrogen atmosphere for 6 h. Then the mixture was diluted with water and extracted with dichloromethane. The organic solvent was removed under vacuum and the residue was purified by flash column chromatography (n-hexane : ethyl acetate 10 : 1) to afford the corresponding (E)-chloroenynes 7a-f.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxyphenylacetylene, and friends who are interested can also refer to it.

Reference:
Article; Chuang, Da-Wei; El-Shazly, Mohamed; Chen, Chin-Chau; Chung, Yu-Ming; D. Barve, Balaji; Wu, Ming-Jung; Chang, Fang-Rong; Wu, Yang-Chang; Tetrahedron Letters; vol. 54; 38; (2013); p. 5162 – 5166;,
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Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

Benzaldehyde (1.58 mL, 15.72 mmol) and 2,2-diethoxyethanamine (3.15 g, 23.58 mmol, 1.5 equiv) were stirred at room temperature for 30 minutes. Triacetoxyborohydride (10 g, 47.18 mmol, 3.0 equiv) was diluted slowly in tetrahydrofuran (150 mL, 10 vol) and slowly added dropwise. The reaction mixture was stirred at room temperature for 12 hours. After the reaction was completed, the mixture was diluted with ethyl acetate (200 mL, 15 vol) and washed once with saturated sodium bicarbonate (200 mL, 15 vol) and water (200 mL, 15 vol). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane: ethyl acetate)=1:1 (v/v) to obtain the target compound (3 g, 87%).

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanmi Pharm Co., Ltd.; Bae In-hwan; Park Chang-hui; Ahn Yeong-gil; (28 pag.)KR2019/40763; (2019); A;,
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Reference of 2688-84-8, These common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, 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.

2-Phenoxyaniline (30 mmol) and triethylamine (31.5 mmol) were dissolved in 100 mL of tetrahydrofuran, and the concentration of 2-phenoxyaniline was 0.3 mol/L. The mixture was cooled in an ice-water bath, and stirred. Then oxalyl chloride (15.8 mmol) was added dropwise. The system turned to turbid and triethylamide hydrochloride was formed. The ice-water bath was then removed and the mixture was warmed to room temperature in the air, and continuously stirred for 2 hours until 2-phenoxyaniline was completely consumed (monitored by TLC). Then the stirring was stopped for post process. The stirring bar was removed by a magnetic bar, and tetrahydrofuran was removed by evaporation under reduced pressure. 50 mL of distilled water was added to the resultant residue. The solid on the flask wall was scraped off and immersed into distilled water, and stirred to form slurry. Et3N.HCl was completely dissolved in water while the oxalic diamide was left undissolved. Then the slurry was filtered under reduced pressure, and the solid on filter paper was washed with cold diethyl ether. The residue was removed and dried in an infrared oven, and then dried with an oil pump to afford a white solid (5.45 g, 86% yield). 1H NMR (400 MHz, CDCl3) delta 9.96 (s, 2H), 8.46 (dd, J=8.0, 1.7 Hz, 2H), 7.43-7.30 (m, 4H), 7.22-7.01 (m, 10H), 6.89 (dd, J=8.0, 1.5 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 157.36, 156.06, 146.73, 129.97, 127.97, 125.40, 124.18, 123.75, 120.49, 119.02, 117.60; HRMS (ESI) calcd. for C26H21N2O4 (M+H)+: 425.1496, Found: 425.1492

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CE Pharm CO., LTD; Ma, Dawei; Zhou, Wei; Fan, Mengyang; Wu, Haibo; Yin, Junli; Xia, Shanghua; (73 pag.)US10500577; (2019); B2;,
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Application of 113421-98-0,Some common heterocyclic compound, 113421-98-0, name is 4-Fluoro-3-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

4-bromo-6-acetylamino-1H-indole-2-carboxylic acid ethyl ester (100 mg, 0.31 mmol), Pd2 (dba) 3 (28 mg, 0.031 mmol), X-phos (30 mg, 0.062 mmol), Cs2CO3 (301 mg, 0.92 mmol) and 3-trifluoromethoxy-4-fluoroaniline (172 mg, 0.92 mmol) were added to a microwave tube, dissolved in 1,4-dioxane (2 mL), and filled with argon Gas-protected, microwave reaction at 100 C for 0.5h, the raw materials disappeared. Cool to room temperature, add EA (20mL), wash with saturated brine (20mL ¡Á 3), wash with water (20mL ¡Á 2), and column chromatography (P / E = 2: 1) to obtain 84mg of a white solid with a yield of 62.2% and a melting point. : 205-206 C.

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

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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Reference of 6793-92-6, These common heterocyclic compound, 6793-92-6, name is 1-Bromo-4-(phenylmethoxy)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.

Nanoporous metal gold catalyst (9.8 mg, 0.05 mmol), ethanol (2 mL) and 4-benzyloxybromobenzene(65.75 mg, 0.25 mmol), cesium carbonate (364.3 mg, 1.125 mmol) was added to the reaction kettle, and hydrogen (40 bar) was added.Heat stirring, the reaction temperature is controlled at 100 C, the reaction time is controlled at 90 h, and the reaction solution is extracted with water to obtain 42.32 mg of biphenyl.The yield was 92%.

Statistics shows that 1-Bromo-4-(phenylmethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 6793-92-6.

Reference:
Patent; Dalian University of Technology; Bao Ming; Zhao Yuhui; Feng Xiujuan; Yu Xiaoqiang; Zhang Sheng; (13 pag.)CN109608297; (2019); A;,
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Electric Literature of 41365-75-7, A common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

N,N-Diisopropylethylamine (3.397 mL, 19.5 mmol) followed by 3,3-diethoxypropan-l- amine (3.154 mL, 19.5 mmol) were added to a solution of 4-chloro-l-fluoro-2- nitrobenzene (1.765 mL, 15 mmol), in iPrOH (35 mL) and heated at 80 C for 4.5 h. After cooling to rt, the reaction mixture was diluted with EtOAc (100 mL) and washed successively with H20 (acidified to ~pH 6 with 0.01 M aqueous HCl, 4chi) and brine (1 x, 100 mL each), dried (MgS04) and the solvent removed under reduced pressure to afford the crude product as an orange solid (4.308 g, 97%). MR (400 MHz, CDC13): delta 8.29 (br s, 1H), 8.17 (d, J= 2.6 Hz, 1H), 7.37 (ddd, J= 9.2, 2.6, 0.6 Hz, 1H), 6.83 (d, J = 9.2 Hz, 1H), 4.65 (t, J= 5.0 Hz, 1H), 3.76-3.65 (m, 2H), 3.59-3.49 (m, 2H), 3.44-3.37 (m, 2H), 2.07-2.01 (m, 2H), 1.24 (t, J= 7.0 Hz, 6H). LRMS (ESI+) m/z 324.9 [M+Na]+ The following intermediate compounds were prepared by the same general procedure.

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; REVIRAL LIMITED; COCKERILL, Stuart George; GOOD, James; (53 pag.)WO2019/16566; (2019); A1;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6BrFO

a) 3-Bromo-6-fluoro-2-methoxybenzoic acid I45 To a solution of diisopropylamine (5.4 g, 53.7 mmol) in THF (150 ml.) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 23.4 ml_, 58.5 mmol) dropwise and the mixture was stirred at -78 C for 1 h. The resulting mixture was added dropwise to a solution of 1-bromo-4-fluoro-2-methoxybenzene (10.0 g, 48.8 mmol) in THF (50 ml.) at -78 C and stirring was continued for 90 min. C02 was bubbled through the mixture for 20 min with stirring at -78 C, then allowed to warm to RT and stirred for 15 min. The reaction mixture was adjusted to pH=1 with HCI and the mixture was diluted with water and extracted with DCM (500 ml_). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH = 100/1 to 30/1) to give the title compound (8.0 g, 66%) as a colorless oil. LCMS-D: Rt2.12 min; m/z 248.9/250.9 [M+H]+.

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: ((3-Bromopropoxy)methyl)benzene

To a solution of methyl [2- (4-HYDROXYPHENOXY)-2-METHYLBUTANOATE] (5g, 22. [32MMOL)] in 30mL [DMF] was added cesium carbonate (8.7g, 26. [7MMOL)] followed by benzyl 3-bromopropyl ether (7.7g, 33.6mmol). The solution was stirred at 45 [XB0;C] for 24hr, cooled and poured over water. Extraction with AcOEt followed by washing the extracts with water, drying over anhydrous [NA2SO4] and concentrating under reduced pressure gave the crude residue. Purification over silica gel using AcOEt/hexanes furnished the desired alkylated derivative (8.25g). This product was taken up in [MEOH] (75mL) and hydrogenated over 10percent [PD/C] at 40psi to provide methyl [2- (4- (3-HYDROXYPROPOXY)] phenoxy) -2-methylbutanoate (6.23g, quantitative). [‘H-NMR] [(400MHZ,] [CDC13)] : [8] 6.82 (d, 2H, J=9.4Hz), 6.78 (d, 2H, J=9.2Hz), 4.08 (t, 2H, J=6. [1HZ),] 3.87 (t, 2H, J=6Hz), 3.79 (s, 3H), 2.06-1. 92 (m, 4H), 1.44 (s, 3H), 0.99 (t, 3H, J=7.4Hz).

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/10992; (2004); A1;,
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Reference of 126-38-5, A common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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.

[0186] A mixture of 3-bromobenzenethiol (630 muL, 5.33 mmol), l-bromo-2,2- dimethoxypropane (715 muL, 5.29 mmol), and K2CO3 (1.10 g, 7.96 mmol) in DMF (11 mL) was heated at 150 0C for 2.5 hours. The crude reaction mixture was cooled, filtered, and concentrated. The residue was purified using flash chromatography (0-30% ethyl acetate in hexanes) to afford the title compound as a clear oil (1.66 g, 108% with some trapped solvent). The material was used as is for the next reaction. [0187] 1H NMR (500 MHz, DMSO-J6) delta 1.33 (s, 3H), 3.12 (s, 6H), 3.25 (s, 2H), 7.25 (dd, J = 8.4, 7.5 Hz, IH), 7.36 (dd, J = 7.9, 1.9 Hz, 2H), 7.54 (t, J= 1.8 Hz, IH)

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; TARGEGEN INC.; WO2009/26345; (2009); A1;,
Ether – Wikipedia,
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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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,2-Diethoxyethanamine

N- (2,2-Diethoxyethyl)carbodiimide; [0077] A solution of the aminoacetaldehyde diethyl acetal (13.16g, 99 mmol) in ether (35 mL) was added to a suspension ofCNBr (10.47g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Purification by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient) afforded the title compound (7.0 g, 44.7%, one half of the starting amine served as a sacrificial base in the reaction) (Rf; 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid). 1H NMR 400 MHz (CDC13) 8 4.58 (t, J= 5.2 Hz, 1H), 3.77 – 3.69 (m, 2H), 3.65 (br, s, 1H), 3.60 – 3.52 (m, 2H), 3.16 (t, J= 5.6 Hz, 1H), 1.23 (t, 6H, J= 6.8 Hz).

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 645-36-3.

Reference:
Patent; IRM LLC; WO2005/123719; (2005); A1;,
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