Ethers-buliding-blocks

A common compound: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. 54149-17-6

(Synthesis of Charge Transporting Compound L); [Show Image] Under nitrogen atmosphere, Compound G (0.17 g, 0.31 mmol) and 9.5 g of N,N-dimethylformamide were placed in a 50-ml three-necked flask, and 0.03 g (0.63 mmol) of sodium hydride (60% oil dispersion) was added thereto. Then, the mixture was stirred for 30 minutes. The temperature was raised to 50C. Then, 0.07 g (0.41 mmol) of the above-described halogen compound K was added dropwise thereto, and the mixture was stirred for 7 hours. The reaction liquid was poured into 20 ml of water, and extraction was performed twice with 20 ml of ethyl acetate. The obtained organic layer was washed twice with 20 ml of water. After the organic layer was concentrated by using an evaporator, the obtained residue was purified by silica gel chromatography (10 g of silica gel was used; elution was performed by using 200 ml of hexane/ethyl acetate =2:1 (volume ratio) ; and further elution was performed by using 200 ml of ethyl acetate). Thus, 0.14 g (Yield: 69.3%) of Compound L was obtained. 1H-NMR (270 MHz, CDCl3): delta 2.01 (m, 2H), 2.89 (t, 2H), 3,37 (s, 3H), 3.48-3.58 (m, 4H), 3.58-3.70 (m, 6H), 7.20-7.35 (m, 4H), 7.35-7.53 (m, 7H), 7.63 (d, 4H), 7.81 (d, 4H), 7.98 (s, 1H), 8.14 (m, 3H)

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, 54149-17-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2116531; (2009); A1;,
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A common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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. 101-55-3.

EXAMPLE 1 1-(2-Methyl-3-butyn-2-ol)-2-(4-phenyloxyphenyl)ethyne Into a 1 L three-necked, round-bottomed flask equipped with a magnetic stirrer, a condenser, and a nitrogen inlet, 4-bromodiphenylether (50.1 g, 201 mmol), freshly distilled 2-methyl-3-butyn-2-ol (64.3 g, 892 mmol), copper(I) iodide (0.11 g, 0.60 mmol), triphenylphosphine (0.33 g, 1.3 mmol), and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.6 mmol) were placed. The solids were carefully washed in with triethylamine (500 mL). The mixture was heated under reflux for 24 h. After the reaction mixture had been allowed to cool to room temperature, the solution was filtered through silica gel. The filtrate was poured into 5% hydrochloric acid solution and diluted with methylene chloride. After separation from the aqueous phase, the organic phase was subjected to purification via a silica-gel column chromatography with methylene chloride/hexane elution to give 40.5 g (80% yield) of light yellow oil. Anal. Calcd. for C17H16O2: C, 80.93%; H, 6.39%; O, 12.68%. Found: C, 80.88%; H, 6.43%; O, 12.89%. Mass spectrum (m/e): 252 (M+, 100% relative abundance).

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

Reference:
Patent; The United States of America as represented by the Secretary of the Air Force; US6979737; (2005); B1;,
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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. 1484-26-0, name is 3-Benzyloxyaniline, A new synthetic method of this compound is introduced below., 1484-26-0

Example 37; Preparation of Intermediate Compound 37C; Step A ~ Synthesis of Compound 37B; Compound 37A (commercially available) (10.0 g, 50.25 mmol) was dissolved in water at room temperature and to resulting suspension K2CO3 ( 3.8 g, 27.64 mmol) was added. 3- Chloro propionylchloride (7.0 g, 55.28 mmol) was added dropwise for 30 minutes and stirred for 2 hours at RT. The precipitate was filtered and washed with water, 1 N HCl, dried at 50 0C under vacuum overnight to give 7.2 g of the product 37B.

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; SCHERING CORPORATION; WO2009/32123; (2009); A2;,
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2674-34-2, A common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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.

1,4-Dibromo-2,5-dimethoxybenzene (2.0 g, 6.76 mmol) was added dissolved in THF 35 mL, it was added dropwise a 1.6 M BuLi slowly at -78 . After stirring the reaction solution for 2 hours at -78 , it was added dropwise to DMF (2.8 mL, 33.7 mmol). The reaction solution is stirred at room temperature for 15 hours (20 ). 2 N HCl in a 20 mL reaction mixture was stirred slowly dropping off. The resulting solid was then filtered under reduced pressure, dried to obtain a 2,5-dimethoxyterephthalaldehyde 267 mg (30%).

The synthetic route of 1,4-Dibromo-2,5-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Lee, Jong Chul; Mun, Sang Jin; Sin, Won Suk; Lee, Sang Gyu; (19 pag.)KR101493823; (2015); B1;,
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Adding some certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3. 74137-36-3

To a solution of 1,3-dibromo-5-methoxy-benzene (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 3-bromo-5-methoxy-benzaldehyde.

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 1,3-Dibromo-5-methoxybenzene.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); A1;,
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Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 105529-58-6, name is 4-Bromo-2-fluoro-1-(trifluoromethoxy)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. 105529-58-6

(Fifth stage) In 80 ml of THF was dissolved 8.0 g (30 mmol) of the 2-(3,5-difluorophenyl)-5-pentylpyrimidine described above, and cooled down to -60 C. under nitrogen gas atmosphere. To this solution was added dropwise 20 ml of 1.60 M solution of n-butyl lithium (32 mmol) in hexane while maintaining the condition that the temperature of the solution did not exceed -50 C., and then stirred at the same temperature for 1 hour. Subsequently, 64 ml of 0.5 M solution of zinc chloride (32 mmol) in THF was added dropwise to the reaction solution while maintaining the condition that the temperature of the solution did not exceed -50 C., warmed up to room temperature, and then stirred for 30 min. To this solution were added 0.5 g of tetrakistriphenylphosphine palladium and 8.3 g of 3-fluoro-4-trifluoromethoxybromobenzene, and heated to reflux for 3 hours. To the reaction solution was added 100 ml of water, and the product was extracted with toluene. The extract was washed with 3N-hydrochloric acid, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride in turn, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: heptane/toluene=1/1), and then recrystallized twice from heptane/ethyl acetate=1/1 to obtain 0.09 g (0.2 mmol) of 2-(4-(3-fluoro-4-trifluoromethoxyphenyl)-3,5-difluorophenyl)-5-pentylpyrimidine. Yield of this product from 2-(3,5-difluorophenyl)-5-pentylpyrimidine was 0.7%.

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 105529-58-6.

Reference:
Patent; Chisso Corporation; US6326065; (2001); B1;,
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. 946-80-5, name is Benzyl Phenyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 946-80-5

Preparation of 4-benzyloxyphenylsulfonyl chloride (24-2) STR187 To a 0 C. solution of sulfonyl chloride (1.9 mL, 23.8 mmol) in 2 mL of DMF was added 4.0 g (21.7 mmol) of benzyl phenyl ether (24-1). The resulting solution was then heated at 100 C. for 2 h. The reaction mixture was then cooled and poured onto crushed ice. The aqueous layer was extracted with CH2 Cl2 (x3). The combined organic extracts were dried (Na2 SO4) and concentrated. Column chromatography (95:5 Hexane/EtOAc) and trituration (hexane) of the pure fractions afforded 24-2 as a pink solid. 1 H NMR (CDCl3) delta 8.00 (d, J=7.8 Hz, 2H), 7.45 (m, 5H), 7.10 (d, J=7.8 Hz, 2H), 5.15 (s, 2H).

The synthetic route of 946-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5872138; (1999); A;,
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Ether | (C2H5)2O – PubChem

1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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.

Step 1. 4-(l-(2-(Benzyloxy)ethyl)-4-(trifluoromethyl)-lH-imidazol-2-yl)benzonitrile (0931) [00299] A mixture of Intermediate B-20 (1 g, 4.22 mmol), ((2-bromoethoxy)methyl)benzene (1.09 g, 5.07 mmol) and cesium carbonate (2.75 g, 8.44 mmol) in DMF (15 mL) was stirred for 18 h at 110 ¡ãC. After cooling to ambient temperature, the reaction mixture was poured into water (100 mL) and was then extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 1.5 g (96percent) of 4-(l-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)-lH-imidazol-2- yl)benzonitrile as a colorless oil. MS (ESI) m/z 371.8 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route ((2-Bromoethoxy)methyl)benzene, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
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20781-20-8, 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.

To a solution of compound 58 (6.6 g, 33.5 mmol) in dichloromethane (100 mL) were added DIPEA (8.65 g, 67 mmol), HOBt (5.4 g, 36.85 mmol) and EDCI (9.6 g, 50.3 mmol). After about 15 min stirring, to the homogeneous reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.6 g, 33.5 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16h. The reaction mixture was washed successively with IN NaOH (100 mL), water (100 mL) and brine (100 mL). The organic phase was then dried over Na2S04 and evaporated to give a crude solid product 59 that crystallized from ethyl ether. Filtration and open air suction drying afforded an off-white solid pure product 9.8g (96%), (MS: [M+l] = 347).

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, (2,4-Dimethoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGENEBIO, INC.; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; WO2015/95783; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

134364-69-5, 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. 134364-69-5, name is 2,3-Difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In 0 C next, the anhydrous aluminum chloride (1.82g, 13mmol) is added to 5-bromo-2-chlorobenzene formyl chloride 12b (3.4g, 13 . 4mmol, see example 12 step 1) and 1,2-difluoro-3-methoxybenzene 14b (2.4g, 16 . 7mmol) in dichloromethane (40 ml) in a mixed solution, in 0 C reaction under 16 hours. Maintain 0 C using hydrochloric acid solution (4 ml, 8mmol, 2M) quenching the reaction, the resulting mixture of natural temperature raising to room temperature, with methylene chloride (40 ml ¡Á 4) extraction, combined with the phase. The organic phase is dried with anhydrous sodium sulfate, filtered, filtrate concentrated to obtain title compound 14c crude product of (5.4g, yellow liquid), yield: 96.4%. The crude product is directly used for the next step synthesis.

The synthetic route of 2,3-Difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Gu, Zheng; Wen, Jiaping; Tang, Wanjun; Wang, Weihua; Deng, Bingchu; Wu, Wuyong; Qu, Tong; (100 pag.)CN105461762; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem