Ethers-buliding-blocks

52189-63-6, These common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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 aluminum chloride (8.6 g, 64.04 mmol) in toluene (30 mL) was added 1-fluoro-3,5-dimethoxybenzene (301-3) (10.0 g, 64.04 mmol) at 0 C. The reaction mixture was stirred for 2 hours. To the above mixture was added acetyl chloride (5.0 g, 64.04 mmol). The resulting mixture was stirred for an additional 0.5 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (hexanes/ethyl acetate: 25/1) to afford the title compound 302-3 as a white solid (2.78 g, 22 % yield). ?H NIVIR (400 1VIHz, CDC13): 2.46 (s, 3H), 3.79 (s, 6H), 6.29 (d, J 10.8 Hz, 2H).

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 52189-63-6.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
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Some common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, molecular formula is C8H7F3O, 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. 402-52-8

Example 11 B: 2′-methoxy-5′-trifluoromethyl-acetophenone was prepared as follow {US2003/0109574): in a water bath at room temperature, to a solution of trifluoromethane sulfonic acid (5 ml, 56.7 mmol) under argon was slowly added a solution of 4-trifiuoromethyl-anisol (2.0 g, 1 1.35 mmol) in acetic anhydride (2.15 ml, 22.7 mmol). The resulting dark mixture was stirred for 3 hours at room temperature then poured onto ice water (26 ml). The product was extracted several times with ether. The ethereal layer was washed with a 10% solution of sodium hydrogenocarbonate, water, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography ove . silica gel (gradient cydohexane/dichloromethane: 0-50%) to yield 2′-methoxy-5′-trifluoromethyi- acetophenone (1.7 g, 67%) as a white solid.1 H NMR : CDCI3 delta (ppm): 8.00 (d, J = 2.3 Hz, 1 H), 7.71 (dd, J = 8.8 Hz, J = 2.3 Hz, 1 H), 7.05 (d, J = 8.7 Hz, 1 H), 3.98 (s, 3H), 2.63 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 402-52-8, its application will become more common.

Reference:
Patent; DOMAIN THERAPEUTICS; PRESTWICK CHEMICAL, INC.; SCHANN, Stephan; MAYER, Stanislas; MORICE, Christophe; GIETHLEN, Bruno; WO2011/51478; (2011); A1;,
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54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a dimethylsalenium suspension (130 mL) of 2,7-dibromo (6.48 g, 20 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium hydroxide (5.61 g, 100 mmol) (0.33 g, 2 mmol) and 1-bromo-2- (2-methoxyethoxy) ethane (8.05 g, 44 mmol) and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was cooled to 0 C, and water (120 mL) was added thereto, followed by neutralization with hydrochloric acid. The organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The crude product was concentrated and purified by silica gel column chromatography (eluent: eluent / ethyl acetate (4/1 – & gt; 3/1)) to give Compound 1 (yield 8.47 g, yield: yellow liquid)80%).

The synthetic route of 1-Bromo-2-(2-methoxyethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; OTA, HIROFUMI; ENDO, TOSHIYUKI; (63 pag.)TW2016/2059; (2016); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, A new synthetic method of this compound is introduced below., 494-99-5

Then, 0.6 mol of the thus-obtained compound (VI-2) was dissolved in a 3.5-fold amount by weight, based on (VI-2), of carbon tetrachloride, and 0.66 mol of bromine gas was blown thereinto under reflux condition while irradiating with a mercury vapor lamp. The blowing was completed in 16 hours. After completion of the reaction, the solvent was distilled off to obtain 3,4-dimethoxybenzyl bromide (VII-2) in 92% yield.

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; Sumitomo Chemical Company, Limited; US4335263; (1982); A;,
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450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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 total of 1.64 ml of diisopropylamine was dissolved in 27 ml of tetrahydrofuran, 6.8 ml of a 1.57 M solution of n-butyllithium in hexane was added at -50C under stirring, and the mixture was stirred at -30C for 30 minutes. After cooling to -60C, 2 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was added and the mixture was stirred at -60C for 1 hour. Then, 1.55 ml of 3-fluoro-benzaldehyde was added, followed by stirring for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated, to give 2.4 g of the title compound as a yellow-brown oil.1H-NMR ( 400 MHz, CDCl3 ) d 3.52 ( 3H, s ), 3.56 ( 1H, d, J = 10.4 Hz ), 6.16 ( 1H, d, J=11.6Hz ), 6.86 ( 1H, t, J = 8.8 Hz ), 6.92 – 6.99 ( 1H, m ), 7.07 – 7.16 ( 2H, m ), 7.30 ( 1H, td, J = 8.0, 6.0 Hz ), 7.51 ( 1H, dd, J = 8.8, 6.0 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 450-88-4.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
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19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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.

Under an atmosphere of nitrogen, in a 100 mL round-bottomed flask at 0¡ã C., 4-bromo-3-methoxyaniline (2 g, 9.9 mmol) and KOH (6.93 ml, 13.9 mmol) were combined with dichloromethane (30 ml) to give a light brown solution. Then 4-bromobutanoyl chloride (1.84 g, 1.15 ml, 9.9 mmol) was added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into 50 ml dichloromethane and extracted with water (3*20 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 30 ml dichloromethane. Then tetrabutylammonium bromide (63.8 mg, 198 mumol) and KOH (50percent, 6 ml) were added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into dichloromethane (50 ml) and extracted with water (3*20 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 50percent EtOAc in heptane). The title compound was obtained as a off-white crystalline (1.92 g, 71.8percent). MS (m/e)=272.1 [M+H]+.

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 19056-40-7.

Reference:
Patent; Hoffmann-La Roche Inc.; Jakob-Roetne, Roland; Wichmann, Juergen; Peters, Jens-Uwe; Jagasia, Ravi; (33 pag.)US2016/326150; (2016); A1;,
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Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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. 5905-69-1

Piperidine-4-carboxylic acid ethyl (3.52mL, 22.9mmol), and 1-Bromo-4- (difluoromethoxy) benzene (4.25g, 19.1mmol) of TorrEne (122 mL) to the solution, sodium tert- butoxide (2.29g, 23.8mmol), palladium acetate (II) (428mg, 1.91mmol), and, tri -tert- butyl phosphine (370muL, 1.52mmol) was added, and 30 minutes at 80 And the mixture was stirred. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the resulting organic layer was washed with saturated brineAfter, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Siri resulting residue wasGel column chromatography [elution solvent: hexane / ethyl acetate = 100 / 0-90Purification by / 10], the title compound (3.17 g, yield: 56%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 111-95-5 as follows. 111-95-5

The product from step 1 (440 mg, 1.36 mmol) was dissolved in DMF (25 mL), treated with HOBt.H2O (624 mg, 4.08 mmol), and EDC.HCl (786 mg, 4.10 mmol) and stirred for 30 min at room temperature. Bis(2-methoxylethyl)amine (620 mL, 559 mg, 4.20 mmol) was added and the resulting mixture was stirred at room temperature for 16 h and concentrated. The residue was partitioned with water and EtOAc. The EtOAc layer was separated and the aqueous was extracted again with EtOAc. The combined organic layers were washed with 0.5 N HCl, saturated sodium bicarbonate, and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford 214 mg of 3-(bis(2-methoxyethyl)amino)-6-bromo-N2,N2,N5,N5-tetrakis(2-methoxyethyl)pyrazine-2,5-dicarboxamide (26% yield) as a brown oil: LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=3.85 min on 30 mm column, (M+H)+=608.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MediBeacon Inc.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (52 pag.)US2019/125902; (2019); A1;,
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A common compound: 111-95-5, name is Bis(2-methoxyethyl)amine, 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. 111-95-5

General procedure: General procedure B: To a mechanically stirred solution of bis(2-methoxyethyl)amine (39.96 g, 0.3 mol) in dichloromethane (100 mL), was added dropwise n-butyllithium (1.6 M in n-hexane, 187.5 mL, 0.3 mol) at -78 C under an argon atmosphere. After further stirring for 5 min, pentafluoroethanesulfonyl fluoride (2, 20.21 g, 0.1 mol) was added and the mixture was stirred for 1 h. Then the cryopump was removed, and allow the mixture stand at room temperature. The subsequent procedures exactly followed those in the procedure A.

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, 111-95-5, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fu, Shi-Tao; Liao, Shuai-Ling; Nie, Jin; Zhou, Zhi-Bin; Journal of Fluorine Chemistry; vol. 147; (2013); p. 56 – 64;,
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134364-69-5, The chemical industry reduces the impact on the environment during synthesis 134364-69-5, name is 2,3-Difluoroanisole, I believe this compound will play a more active role in future production and life.

The first step: 1000mL four-neck flask, equipped with a thermometer and a condenser tube, under nitrogen protection, put in 2,3-difluoroanisole 57.6g (0.4mol) and 440mL of tetrahydrofuran, start stirring, and lower the temperature to -85 At -75 C, 192 mL (0.48 mol) of n-butyl lithium in hexane solution (2.5 mol / L) was slowly added dropwise. After the addition was completed, the temperature was controlled and stirred for 2.0 hours. After the heat preservation is completed, the temperature is controlled from -85 C to -75 C, and 62.3g (0.6mol) of trimethyl borate is added dropwise. Sample delivery liquid phase detection of 2,3-difluoroanisole raw material residue <0.5%.After the reaction is completed, dehydrolyze tetrahydrofuran under negative pressure until the temperature of the reaction flask reaches 50 C without flow, stop the desolvation, cool to 20-25 C, add 520mL of pure water, control temperature 20-25 C and drop 133.3g (1.0 mol), the dropwise addition was completed and kept stirring for 1.0 hour. 172.8g toluene was added for extraction, the toluene phase was stored separately for use, and the aqueous phase was directly oxidized without further purification. Recover 430.5g of desolvent, send sample to detect water 0.02%, tetrahydrofuran: n-hexane mass ratio is about 4: 1, methanol content is 1.5%, need to remove methanol to apply. The chemical industry reduces the impact on the environment during synthesis 2,3-Difluoroanisole. I believe this compound will play a more active role in future production and life. Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Xu Jianxiao; Liu Hongqiang; Zhao Shimin; Wei Jiayu; Wang Songsong; Zhu Keming; (7 pag.)CN110922306; (2020); A;,
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