Category: ethers-buliding-blocks

366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-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.

To cyanuric chloride(0. 368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39mL, 2.2 mmol) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg,30percent), mp91-92 C ; HPLC : Inertsil ODS-3V C18, 40: 30: 30[KH2PO4(0. 01 M, pH3. 2):CH30H : CH3CN], 264nm, Rt 8.6 min, 99.1percent purity; MS(ESI) : m/z 331 (M+H, 100), 305 (0.8), 151 (. 3).

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 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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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 126-38-5 as follows. 126-38-5

To a solution of 4-bromopyridin-2-amine (1.08 g, 6.24 mmol) in H20 (20 mL) were added l-bromo-2,2-dimethoxypropane (5.59 g, 30.5 mmol) and 4-methylbenzenesulfonic acid (209.4 mg, 1.216 mmol). The reaction mixture was heated to reflux and stirred for 12 hours and then adjusted to pH = 10 with saturated Na2C03 aqueous solution, the resulting mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc(v/v) = 3/1) to give the title compound as a yellow solid (750 mg, yield 57%).MS (ESI, pos. ion) m/z: 211.1 [M+H]+.

According to the analysis of related databases, 126-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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1535-73-5, 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 1535-73-5 as follows.

General procedure: Two mmol 5b1?5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 ¡ãC. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 ¡ãC. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1?6b20.

According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
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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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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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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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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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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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111-95-5, Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5.

To the product from step 2 (1.00 g, 5.29 mmol) in ACN (20 mL) was added bis(2- methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 0C for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCI3) .delta 7.47 (bs, 2 H), 3.77 (t, J = 5.7 Hz, 4 H)1 3.52 (t, J = 5.4 Hz, 4 H), 3.25 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 154.7 (s), 152.0 (s), 120.9 (s), 1 19.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t). LCMS (50-95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 4.91 min on 250 mm column, (M+H)+ = 286, (M+Na)+ = 308, (M+Na+ACN)+ = 349.

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
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A common compound: 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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. 19056-40-7

POCl3 (5.07 mL, 54.4 mmol) was added to a mixture of 4-bromo-3- methoxyaniline (10 g, 49.5 mmol) and malonic acid (5.15 g, 49.5 mmol) with thorough mixing, and the mixture was then heated to 105¡ãC. After 5 minutes, the reaction began to bubble vigorously, and eventually formed a hard foam; heating was continued for 1 hour. After cooling, water (200 mL) was added, and the mixture was stirred for 30 minutes. The solid was filtered off and washed with water. 2N NaOH (300 mL) was added to the solid, and stirring was continued overnight. The remaining solid was filtered off; EtOH (5 mL) was then added to the filtrate; and the basic layer was then acidified with concentrated HCl to pH 2. The resulting solid was then filtered off, washed with water. The solid was then transferred to a flask, and the remaining water was removed by stripping off EtOH (200 mL x 2). The solid was then further dried under high vacuum for 15 hours to yield 8.75 g (66percent) of the title compound as an off- white solid. LRMS ESI+ (M+H)+ 270.2/272.2.

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, 19056-40-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/51514; (2008); A2;,
Ether – Wikipedia,
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