Ethers-buliding-blocks

1758-46-9, Adding some certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9.

To a stirred yellow solution of VII (371.8 mg, 1.089 mmol) in anhydrous THF (10 mL) was added 2-phenoxyethylamine (165 mg, 157 muL, 1,1×1.089 mmol) and then, dropwise, triethylamine (121 mg, 168 muL, 1.1×1.089 mmol). The solution was stirred for 1.5 hours at room temperature. The colorless solution was then diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to yield 260.6 mg (67percent) of a 11 as a clear light yellow oil: Rf=0.39 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) delta 7.26 (td, 3J=8.0 Hz, 4J=1.1 Hz, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.96 (m, 1H), 6.94 (d, 4J=1.0 Hz, 1H), 6.92 (dd, 3J=8.7 Hz, 1H), 6.86 (d, 3J=8.1 Hz, 2H), 5.21 (bs, 1H, NH), 5.06 (s, 2H), 4.03 (t, 3J=5.0 Hz, 2H), 3.80 (s, 3H), 3.59 (q, 3J=5.2 Hz, 2H, NCH2) and 2.29 (s, 3H). Exact mass (EST) calculated for C19H22NO6 [M+H]=360.1442. found 360.1443.

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 1758-46-9.

Reference:
Patent; Laskin, Jeffrey D.; Heck, Diane E.; Lacey, Carl Jeffrey; Aponte, Erik; Huang, Mou-Tuan; Heindel, Ned D.; US2012/59007; (2012); A1;,
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These common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, 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. 887581-09-1

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 ¡Á 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

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 887581-09-1.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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. 6851-80-5

Step B: To an ice-cooled mixture of the product from Step A (348 mg, 2.3 mmol) and diisopropylethylamine (394 mg, 3.0 mmol) in dichloromethane (10 mL) was added 1-(benzothiophen-5-yl)-2-bromo-ethanone (see Example 96 for preparation) (600 mg, 2.03 mmol). The reaction mixture was stirred at room temperature for 4 hours and then diluted with dichloromethane (100 mL). The mixture was washed with water and brine, dried over sodium sulfate and concentrated to provide the desired product (800 mg, >99% crude yield): ESI-MS m/z=326 [M+H]+. This crude product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6851-80-5, its application will become more common.

Reference:
Patent; Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.; US2006/52378; (2006); A1;,
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A common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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. 102-52-3.

5-Amino-1H-pyrazole-4-carboxylic acidEthyl ester (3.0 g, 19.3 mmol)In acetic acid (40 mL) and ethanol (10 mL)1,1,3,3-Tetramethoxypropane (3.48 g, 21.4 mmol) was added,The resulting reaction was stirred at 90 C overnight,Cool to room temperature,Concentrate under reduced pressure.The resulting residue was diluted with ethyl acetate (100 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (DCM / EA v / v) = 6/1) to give the title compound as a light yellow solid (3.2 g, 85%).

The synthetic route of 1,1,3,3-Tetramethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
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A common compound: 645-36-3, name is 2,2-Diethoxyethanamine, 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. 645-36-3

A suspension of pyrimidine 116 (0.5 g, 2.27 mmol) in MeOH (25mL) was treated by dropwise addition of a soln of 2,2-diethoxyethylamine(395 muL, 23 mmol) in MeOH (5 mL). Na2CO3 (0.29 g,2.73 mmol) was added and the mixture was stirred at r.t. for 1 h.H2O (100 mL) was then added and the resulting precipitate was collectedby filtration, dried, and crystallized (hexane) to give a colorlesssolid; yield: 0.53 g (74%); mp 74-75 C.IR (KBr): 3332 (NH), 2222 (CN) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.28 (t, J = 6.9 Hz, 6 H, 2 ¡Á CH3),2.56 (s, 3 H, SCH3), 3.60 (dq, 2J = 9.6 Hz, 3J = 6.9 Hz, 2 H,2 ¡Á CHAHBCH3), 3.70-3.84 (m, 4 H, NCH2 and 2 ¡Á CHAHBCH3),4.64 (t, J = 5.4 Hz, 1 H, OCH), 5.89 (t, J = 5.4 Hz, 1 H, NH).13C NMR (75 MHz, CDCl3): delta = 14.7, 15.6, 44.0, 63.5, 86.1, 100.2,113.8, 161.2, 161.5, 176.3.Anal. Calcd for C12H17ClN4O2S: C, 45.49; H, 5.41; found: C, 45.62;H, 5.57.

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, 645-36-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., 768-70-7

At room temperature, FTA-Au(I)catalyst (2 mol%), AgOTf (5 mol%) was added to a stirring solution of 6a (1.0 mmol) in HOAc/H2O(10:1, 4 mL), then the reaction mixture was heated to 100 oC andstirred overnight (12 h). After the reaction completed, the solvent was removedunder reduced pressure and the residue was purified by flash chromatography onsilica gel (ethyl acetate/hexane = 1 : 80, V/V) to give the title compound 7a in 89% yield as light yellow oil.

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:
Article; Yao, Wei; Zhang, Yilin; Xu, Xiaqing; Yang, Yongchun; Zeng, Wei; Wang, Dawei; Journal of Organometallic Chemistry; vol. 901; (2019);,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 5961-59-1

27.4 mg (0.2 mmol) of N-methyl-4-methoxyaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid N-(4-methoxyphenyl)-N-methylformamide 26.4 mg, yield 80%.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
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20265-97-8, These common heterocyclic compound, 20265-97-8, name is 4-Methoxyaniline hydrochloride, 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.

p-anisidine hydrochloride (0.01 mol) was dissolved in a solution of concentrated hydrochloric acid (0.02 mol) in 50 ml of water. The mixture was cooled to 273 K on an ice water bath, and then sodium nitrite (0.015 mol) was dissolved in a small amount of water and added dropwise with vigorous stirring. The reaction mixture was stirred for1h, and then ethylenediamine dihydrochloride (0.0025 mol) was added. After the intense stirring for 10 min, KOH (0.04 mol) in 100 ml of water was added dropwise.The reaction took place immediately, and, as a result, the solution changed its color.The precipitate was collected by the vacuum filtration and dried at room temperature in vacuum. Yield 80%.1H-NMR (400 MHz, DMSO-D6, d, ppm) 7.50 (d, 8H, Ar), 6.90 (d, 8H, Ar), 3.84 (s,12H, -CH3), 3.1 (s, 4H, -CH2-) IR (KBr): 3000, 2934, 1602, 1504, 1448, 1248, 1028, 834

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 20265-97-8.

Reference:
Article; Vyshnevsky, Dmitry; Syromyatnikov, Vladimir; Kolendo, Alexey; Molecular Crystals and Liquid Crystals; vol. 672; 1; (2018); p. 73 – 80;,
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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. 454-90-0 name is 3-(Trifluoromethyl)anisole, 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. 454-90-0

General procedure: (b) For isolations of the major products, copper(I) chloride (0.248 g, 2.5 mmol) and Mg powder (0.486 g, 20 mmol) were stirred in DMI (20 ml, 10 ml for 7i, 7j, 7k) and TMS-Cl (5 ml, 40 mmol) for 15 min under an argon atmosphere. Then, a benzotrifluoride derivative 6 (5 mmol) was added dropwise over 5 min into the dark suspension. The solution was stirred for additional time (see Table 2), keeping the temperature 25 C (bath temperature, 50 C for 7i, 7j, 7k). After addition of 5 ml of hexane, Mg-Cu was removed by decantation and the suspension was simultaneously extracted with hexane (5 ml¡Á5). Then, the combined hexane layer was washed with 10 wt % HCl aq and brine. After drying over sodium sulfate, purification by column chromatography on silica gel (hexane eluent) and distillation afforded the product.

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

Reference:
Article; Utsumi, Shinya; Katagiri, Toshimasa; Uneyama, Kenji; Tetrahedron; vol. 68; 4; (2012); p. 1085 – 1091;,
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101-55-3, 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. 101-55-3, name is 1-Bromo-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4B. Alternative Preparation of (5) where R 5 is 4-(4-Bromophenoxy)phenyl A solution of 4-bromodiphenyl ether (50 g, 200.7 mmol) in methylene chloride (118 ml) was cooled to 0C and chlorosulfonic acid (14.7 ml, 220.8 mmol) was added dropwise over a 20 minute period. The solution was stirred an additional 10 minutes, warmed to room temperature and stirred an additional 1 hour. To this mixture was added oxalyl chloride (23.6 ml, 270.9 mmol), followed by N,N-dimethylformamide (1.5 ml) as a catalyst, and the mixture refluxed for 2 hours. The mixture was cooled to room temperature, and additional oxalyl chloride (23.6 ml, 270.9 mmol) was added, the mixture refluxed for 3 hours, cooled to room temperature and stirred 12 hours more. The solution was concentrated to an oil, azeotroped several times using methylene chloride and put under high vacuum (1 torr) for several hours until the mixture had completely solidified. This mixture was immediately dissolved in methylene chloride (160 ml) which was added dropwise to a solution of triphenylphosphine (157.0 g, 602 mmol) in methylene chloride (160 ml) containing N,N-dimethylformamide (4 ml, 52.2 mmol). The mixture was stirred 2 hours, diluted with 1M aqueous hydrochloric acid (300 ml) and stirred for 1 hour. The aqueous layer was separated, extracted with methylene chloride (200 ml), and the organic layers were combined, washed with 200 ml of brine, dried (MgSO4) and concentrated in vacuo.The resulting solid was further purified through trituration with 750 ml of hexane. The solid was then dissolved in 750 ml of diethyl ether, extracted with 2M aqueous sodium hydroxide (2 x 350 ml), and the basic aqueous layer back extracted using diethyl ether (2 x 400 ml). The aqueous layer was adjusted to pH 2, extracted with diethyl ether (3 x 200 ml) and the combined organic layers dried (MgSO4) and concentrated to afford 4-(4-bromophenoxy)thiophenol (45.6 g, 81%). 1H-NMR (CDCl3) delta 3.43 (s, 1H), 6.86 (d, J= 8.9 Hz, 2H), 6.89 (d, J= 8.6 Hz, 2H), 7.28 (d, J= 8.6 Hz, 2H), 7.43 (d, J= 8.9 Hz, 2H).

The synthetic route of 1-Bromo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AGOURON PHARMACEUTICALS, INC.; EP780386; (1997); A1;,
Ether – Wikipedia,
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