Ethers-buliding-blocks

Application of 70627-52-0, A common heterocyclic compound, 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, molecular formula is C20H16FNO, 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.

Preparation of TiCl4+Ti(O-i-Pr)4 mixed solution:The TiCl4 (21.3g, 0.112mol) dissolved in 100ml dichloromethane.Ti(O-i-Pr)4 (10.6 g, 0037 mol) was added dropwise at 0 C.The reaction was kept for 30 minutes.Intermediate A1-2 (53.4 g, 0.1 mol) andIntermediate A1-3 (61.4 g, 0.2 mol)Soluble in 250ml dichloromethane,DIPEA (25.8g, 0.2mol) was added dropwise at -15 C.TiCl4+Ti(O-i-Pr)4 mixed solution,After the addition is completed, the reaction is continued for 2 hours.Then glacial acetic acid (30 g, 0.5 mol) was added dropwise.After cooling in an ice bath, the reaction solution was poured into a 7% aqueous solution of tartaric acid.Stir for 1 h, naturally warm to room temperature,Add 100ml of 20% sodium bisulfite solution,Stirring was continued for 2 h, the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated.50 ml of methanol was beaten and the white solid was 62.1 g.

The synthetic route of 70627-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuxi Fuqi Pharmaceutical Co., Ltd.; Wang Qinglin; Wang Tao; Wang Binbin; Sun Yilin; (11 pag.)CN109369491; (2019); A;,
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Application of 93-04-9, These common heterocyclic compound, 93-04-9, name is 2-Methoxynaphthalene, 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.

EXAMPLE 1 The following is a procedure for preparing 2-methoxy-6-ethylnaphthalene by the transethylation of 2-methoxynaphthalene. To a 250 ml., 3-neck, round-bottom flask equipped with a magnetic stirrer and a sparge tube were added 70 g of mixed diethylbenzenes obtained from the Aldrich Chemical Company, Milwaukee, Wis. After cooling the reaction mixture with an ice bath, hydrogen chloride gas was added for three minutes and thereupon 14.48 grams of aluminum chloride were slowly added. Hydrogen chloride gas was again added for three minutes. The reaction flask was then placed in a hot water bath to raise the temperature of the reaction mixture to 85-90 C. At this point ethylene gas was sparged into the reaction mixture until the level of tetraethylbenzene in the reaction mixture was maximized. The composition of the mixture was monitored by gas chromatography. After the ethylene addition was stopped, the reaction mixture was stirred for an additional 30 minutes at 90 C. To the above reaction mixture at 15 C. was added a mixture of 29.02 grams of 2-methoxynaphthalene dissolved in 50 ml of dichloromethane. The reaction mixture was permitted to warm to room temperature and after 900 minutes it was heated to 32 C. using a water bath. After 15 hours total reaction time the yield of 2-methoxy-6-ethylnaphthalene was 71.5% as measured by gas chromatography. This example shows the high yield of 2-methoxy-6-ethylnaphthalene that can be achieved by the method of this invention.

Statistics shows that 2-Methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 93-04-9.

Reference:
Patent; Amoco Corporation; US5235115; (1993); A;,
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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. 1579-40-4, name is Di-p-tolyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Di-p-tolyl Ether

1.9827 g (0.01 mol) of dissolved p-tert-phenyl ether,0.01883 g (1 mol%) of Tris derivative modifiedFe-Anderson type polyacid ([N(C4H9)4] 3[FeMo6O18{(OCH 2)3CNH2}2]),0.0106 g (0.1 equiv) of sodium carbonate additive,30% by weight of hydrogen peroxide containing 0.03 moles of hydrogen peroxide and 30 ml of solvent diethyl malonate are put into a dry and clean pressure tube.After heating to 100 C,After 18 hours of heat treatment under a pressure (gauge pressure) of 1.0 MPa,Stop the reaction,The reaction system was extracted 3 times with ethyl acetate.The obtained product is removed under reduced pressure,Column chromatography to obtain 4,4′-diphenyl ether dicarboxylic acid,Obtained 2.3983 grams of product,The yield was 93%.

The synthetic route of 1579-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Technology; Yu Han; Wang Jingjing; He Huihong; (8 pag.)CN108484381; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 768-70-7, name is 3-Ethynylanisole, 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 768-70-7, category: ethers-buliding-blocks

General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3¡Á8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample. 4.2.8. 1-(3-Methoxyphenyl)ethanone (2h). 1H NMR (400 MHz, CDCl3): delta=7.41-7.47 (m, 2H), 7.26-7.31 (m, 1H), 7.02-7.04 (m, 1H), 3.77 (s, 3H), 2.51 (s, 3H). 13C NMR (100 MHz, CDCl3): delta=197.7, 159.7, 138.4, 129.5, 121.0, 119.4, 112.3, 55.3, 26.6. MS (EI) m/z: 150, 135, 107, 92, 77, 63.

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

Reference:
Article; Chen, Zheng-Wang; Ye, Dong-Nai; Qian, Yi-Ping; Ye, Min; Liu, Liang-Xian; Tetrahedron; vol. 69; 30; (2013); p. 6116 – 6120;,
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934240-59-2, name is 1-((4-Bromophenoxy)methyl)-2-fluorobenzene, 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. Recommanded Product: 934240-59-2

To a stirred suspension of magnesium metal (9Og) in dry THF (60OmL) under a nitrogen atmosphere at room temperature was added iodine (0.3g). The mixture was heated to an internal temperature of 64 +/- 2C. A solution of 1-[(4- bromophenoxy)methyl]-2-fluorobenzene (693g) in THF (150OmL) was added in two batches. Firstly 45 mL was added. Secondly, the remaining solution (1455 mL) was added dropwise. After addition, the reaction was heated at reflux for 1 h. The reaction mixture was cooled to room temperature. This reaction mixture was then added slowly to a solution of commercially available 1-te/t-butyl 2-methyl (2S)-5-oxopyrrolidine-1 ,2- dicarboxylate (30Og) in THF (150OmL) cooled to -6O0C, maintaining the internal temperature below -600C. The addition was completed in 2 hours. The reaction mixture was stirred for a further 15 minutes after addition, lsopropyl alcohol (30OmL) was then added dropwise whilst maintaining the temperature below -600C. A mixture of aqueous saturated ammonium chloride solution/aqueous saturated sodium chloride solution (2/1 ; 90OmL) was added whilst maintaining the temperature at -500C. Water (600 ml.) was added to dissolve the yellow precipitate. The organic phase was separated and was washed with aqueous 13% NaCI solution (60OmL). The organic phase was concentrated to dryness. EtOAc (150OmL) was then added and the solution was evaporated under reduced pressure to remove water. The residue was purified by chromatography on silica gel eluting with cyclohexane / ethyl acetate (90:10 to 8:2) to afford the title compound (287 g); 1H NMR (600 MHz, DMSO-d6) delta(ppm): 7.93 (d, 2H); 7.57 (td, 1 H); 7.44 (m, 1 H); 7.27 (m, 3H); 7.14 (d, 2H); 5.24 (s, 2H); 4.04 (m, 1 H); 3.61 (s, 3H); 3.03 (m, 2H); 1.94 (m, 2H); 1.38 (s, 9H).

The synthetic route of 934240-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); 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. 15268-07-2, name is 3,3′-Oxydianiline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 15268-07-2

To a suspension of p-toluenesulfonic acid hydrate (30.8 g, 162 mmol) in tert-butylalcohol (110 mL) and water (5 mL) was added 3,3?-oxydianiline (3.6 g, 17.9 mmol) and the reaction mixture cooled to 10 C. in an ice/water bath. A solution of sodium nitrite (7.4 g, 108 mmol) and potassium iodide (22.4 g, 135 mmol) in water (30 mL) was added dropwise over 1 hour, keeping the temperature below 15 C. The cold bath was removed and the reaction mixture allowed to warm to room temperature and stirred for another 3 hours. To the reaction mixture was added 15 g NaHCO3 to pH 8 followed by 35 g Na2S2O3 and the mixture stirred for 30 minutes before being poured into 300 mL of water. The mixture was extracted 2¡Á100 mL with ether and 3¡Á100 mL DCM. The combined extracts were washed with 2¡Á100 mL water, dried over sodium sulfate and evaporated leaving 4.5 g of a dark liquid. The crude oil was chromatographed on silica with hexane to give 4.8 g (79%) of 3,3?-oxybis(iodobenzene) as a white solid. The product was confirmed by GC/MS and NMR.

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 15268-07-2.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; Tsai, Jui-Yi; Kottas, Gregg; Brooks, Jason; Yeager, Walter; Ansari, Nasrin; Barron, Edward; Xia, Chuanjun; (126 pag.)US9461254; (2016); B2;,
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Reference of 2688-84-8,Some common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, molecular formula is C12H11NO, 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 (25.0, 0.135 mol) and 30 ml of hydrochloric acid were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 C and stirred for 1 hour.75 ml of an aqueous solution of sodium nitrite (11.2 g, 0.162 mol) was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour.When the aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the temperature of the reaction solution was prevented from exceeding 5 and dropping.The mixture was stirred at room temperature for 5 hours and washed with an aqueous sodium thiosulfate solution after completion of the reaction, followed by extraction with ethyl acetate and water.The organic layer was separated and concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate 5-a (22.6 g, 56.5%).

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

Reference:
Patent; SFC Co., Ltd.; Che Chunxu; Po Xipei; Po Shangyu; Shen Youna; Jin Xida; (130 pag.)CN107207454; (2017); A;,
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Related Products of 10103-06-7, A common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

(a) 1-(6,7-Dimethoxy-naphthalen-2-yl)-heptan-1-one Aluminium chloride (2.66 g) was added to a solution of: heptanoylchloride (3.1 ml) and 2,3-dimethoxynaphthalene (3.76 g) in methylene chloride (50 ml) at 0 C. The reaction mixture was stirred at room temperature overnight and then worked up as described in example 3(a). The crude product was recrystallized from ethanol. Yield: 2.8 g, melting point 77-78 C. 1H-NMR (DMSO-d6, 400 MHz): 8.49 (s,1H), 7.81 (s,2H), 7.51 (1H); 7.18 (s,1H), 3.92 (s,3H), 3.91 (s,3H), 3.07 (t,2H, J=8 Hz), 1.61-1.68 (m,2H), 1.29-1.37 (m,8H), 0.87 (t,3H, J=8 Hz).

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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 1535-75-7, Safety of 2-(Trifluoromethoxy)aniline

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3¡Á25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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Reference of 4393-09-3, 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. 4393-09-3 name is (2,3-Dimethoxyphenyl)methanamine, 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: To a suspension of ethyl 4-trifluoromethoxybenzimidate hydrochloride salt (8) (1 equiv) in ethanol (0.25 M) was added the appropriate amine (0.9 equiv). Triethylamine (3 equiv) was added and the resulting reaction mixture stirred at ambient temperature for 16 h. The reaction mixture was then concentrated and the crude product purified by flash chromatography on silica.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,3-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Beinat, Corinne; Banister, Samuel D.; Hoban, Jane; Tsanaktsidis, John; Metaxas, Athanasios; Windhorst, Albert D.; Kassiou, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 828 – 830;,
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