Month: January 2021

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 398-62-9 as follows. HPLC of Formula: C8H9FO2

EXAMPLE 118 4-Chloro-1-[3,4-dimethoxy-6-fluorophenyl]-1-hexanone A solution of 0.1056 g (0.64 mmol) of 4-fluoroveratrole in 1 mL of methylene chloride was added to a mixture of 0.2289 g (1.7 mmol) of aluminum chloride and 0.09 mL (0.8 mmol) of 4-chlorobutyryl chloride in 2 mL of methylene chloride at 25. The reaction mixture was stirred at 25 for 22 hours. Water was added and the organic layer was separated and washed with sodium bicarbonate solution. The dried extract was concentrated under reduced pressure to an oil which was chromatographed on 10 g of silica gel using 25% ethyl acetatehexane to give 0.041 g, mp 81-82, of 4-chloro-[3,4-dimethoxy-6-fluorophenyl]-1-hexanone. The nmr spectrum was consistent with the structure and the mass spectrum gave the molecular ion at m/z 260 (C12 H14 ClFO3)

According to the analysis of related databases, 398-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US5025036; (1991); A;,
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Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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 7252-83-7, Quality Control of 2-Bromo-1,1-dimethoxyethane

To a solution of 4-(diethylamino)benzothioamide (2.29 g, 11 mmol) in EtOH (60 mL) were added 2-bromo-1,1-dimethoxyethane (1.86 g, 11 mmol) and p-toluenesulfonic acid (1.89 g, 11 mmol). The reaction mixture was heated at 95 C. overnight, then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc/Et3N (V/V/V)=2:1:0.05) to give the title compound as a white solid (1.40 g, 55%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,1-dimethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Ether – Wikipedia,
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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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, A new synthetic method of this compound is introduced below., Product Details of 701-07-5

An Et2O solution (10 mL) of I2 (1.21 g, 4.78 mmol) was added to a solid of 1 (0.72 g,0.79 mmol) to prepare the solution of diiodophenylarsine (2). Without isolation, thesolution of 2 was employed the subsequent reaction. To an Et2O solution (10 mL) of1-bromo-2-isopropoxybenzene (1.6 mL, 9.97 mmol) was added a hexane solution ofn-butyllithium (1.6 M, 6.0 mL, 9.6 mmol) at 0 C under N2 atmosphere, and the reactionmixture was stirred at the ambient temperature for 1 h. To the reaction mixture was thesolution of 2 was added at 0 C. The reaction temperature was raised to the ambienttemperature, and the reaction mixture was stirred for 5 h. The reaction was quenchedby distilled water (20 mL), and the products were extracted with EtOAc. The combinedorganic layers were dried over MgSO4, and volatiles were removed in vacuo. The residuewas subjected to recrystallization from EtOH, and washed with MeOH to obtaincolorless solids of 3c (1.52 g, 3.61 mmol, 72%). 1H NMR (CDCl3, 400 MHz) delta 7.34-7.24 (m,7H), 6.86 (t, J = 8.4 Hz, 2H), 6.83-6.77 (m, 4H), 4.50 (sep, J = 6.0 Hz, 2H), 1.18 (d, J = 6.0Hz, 6H), 1.08 (d, J = 6.4 Hz, 6H) ppm; 13C NMR (CDCl3, 100 MHz) delta 159.6, 139.9, 134.4,129.5, 129.4, 128.2, 127.9, 120.7, 112.1, 70.2, 21.9, 21.7 ppm. HR FAB-MS (m/z):calculated for C24H27O2As [M]+; 422.1227, observed; 422.1211.

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:
Article; Imoto, Hiroaki; Yamazawa, Chieko; Tanaka, Susumu; Kato, Takuji; Naka, Kensuke; Chemistry Letters; vol. 46; 6; (2017); p. 821 – 823;,
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Electric Literature of 41406-00-2,Some common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, 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.

EXAMPLE 11 Preparation of 3′-iso-propoxy-2-methylbenzanilide A 13.6 g (0.1 mol) portion of o-methylbenzoic acid, 15.1 g (0.1 mol) of m-isopropoxyaniline and 10.1 g (0.1 mol) of triethylamine were dissolved in 100 ml of xylene. A 5.1 g (0.033 mol) amount of phosphorus oxychloride was added dropwise to the prepared solution with stirring at 90-100C. Stirring of the resulting solution was continued at 90-100C for 3 hours. The reaction mixture was cooled and washed with water, and the product was dried over anhydrous sodium sulfate. The xylene was removed to obtain 20.9 g (77.9%) of white prismatic crystals having a melting point of 92-94C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Isopropoxyaniline, its application will become more common.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; US3937840; (1976); A;,
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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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 126-38-5

2-aminc-5-brcmcpyrazine (lOg, 57mmcl) and 1-brcmc-2,2-dimethcxy-prcpane (15 g) were dissolved in IPA (30 mL) and heated at 100 00 in a sealed tube for 3 days. The reactionwas quenched with sodium bicarbonate solution and filtered and extracted with ethyl acetate;the organic layer was dried over sodium sulphate and concentrated to give a brown solid that was used for the next step without further purification.

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; MERCK PATENT GMBH; GARDNER, John Mark Francis; BELL, Andrew Simon; (87 pag.)WO2020/16235; (2020); A1;,
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Synthetic Route of 454-90-0, A common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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 stirred solution of 1-methoxy-3-(trifluoromethyl)benzene (9.8 mL, 68 mmol) in 50 mL THF under N2 at O0C was added n-BuLi (1.6 M in hexanes, 45 mL, 68 mmol) dropwise. The reaction mixture was stirred at O0C for 2 h, then triisopropylborate (11.6 ml_, 68 mmol) was added. The reaction mixture was slowly warmed up to room temperature and stirred overnight. A solution of 10% HCI in water was added and the mixture was stirred for 1 h. The mixture was extracted with CH2CI2 (3X), The organic layers were combined, washed with brine and dried over Na2SO4 to give 8.14 g of 2-methoxy-4-(trifluoromethyl)phenylboronic acid as a viscous oil. The crude was directly used in the next step without further purification.

The synthetic route of 454-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
Ether – Wikipedia,
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Application of 5467-58-3, 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 5467-58-3 as follows.

To a solution of 1-bromo-4-methoxynaphthalene (4.72 g, 20 mmoL) in 1, 4-dioxane /H2O (80 mL/20mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (5.32 g, 10 mmol), Pd (dppf) Cl2 (1462 mg, 2.0 mmol) and Cs2CO3 (9.75 g, 30 mmol) and the mixture was heated at 70 for 5 hours. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA=5: 1) to give product as an oil (4.1 g in 69% yield). [M+H] +=297.

According to the analysis of related databases, 5467-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
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Synthetic Route of 402-52-8,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.

2-methoxy-5-(trifluoromethyl)benzoic acid (12-3). nBuLi (276 mL, 2.5 M, 0.69 mol, 1.1 equiv) and KOtBu (77 g, 0.69 mol, 1.1 equiv) were added to a THF solution (1 L) of crude 12-2 (110 g) at -78 0C. The reaction was stirred at -78 0C for 4 h. Dry CO2 was bubbled into the solution at -78 0C for 1 h. The reaction was allowed to warm to 25 0C over 0.5 h. NaOH (6N, 300 mL) and H2O were added to the resulting reaction mixture. The mixture was extracted with t-butylmethyl ether (400 mL x 2). The aqueous layer was acidified with HCl (6N) to pH 1 and extracted with EtOAc (300 mL x 4). The combined EtOAc extracts were concentrated and re- dissolved in CH2Cl2. The solution was dried (Na2SO4), filtered through a pad of Celite and concentrated. Flash chromatography on silica gel (1:1 PE/EtOAc) yielded 82 g of compound 12-3 (53% for 2 steps): 1H NMR (400 MHz, CDCl3) delta 8.45 (s, 1 H), 7.81 (d, J= 8.0 Hz5 1 H), 7.16 (d, J= 8.0 Hz5 1 H), 4.13 (s, 3 H); MS (ESI) m/z 221.0 (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 1-Methoxy-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; TETRAPHASE PHARMACEUTICALS, INC.; DENG, Yonghong; PLAMONDON, Louis; SUN, Cuixiang; XIAO, Xiao-Yi; ZHOU, Jingye; SUTCLIFFE, Joyce, A.; RONN, Magnus, P.; WO2011/25982; (2011); A2;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 103291-07-2

In a 1 I three necked round bottom flask, flame dried, under argon, 2-fluoro-5-bromoanisole (27.40 g; 133.64 mmol; 1.20 eq.) was diluted in THF (200 mL) and the mixture was cooled to -78C. Then, n-Butyllithium 1.6M in hexane (98.0 mL; 1.6 mol/L; 156.8 mmol; 1.41 eq.) was slowly added during 20 min, keeping temperature below -65C and the reaction was stirred at -78C for 1h. Next, a solution of 4-chloro-N-methoxy-N-methyl-pentanamide (20.00 g; 111.33 mmol; 1.00 eq.) in THF (100 mL) was slowly added to the lithiated species during 25 min, keeping temperature below -65C. The reaction was then stirred 40 min at -78C and quenched by addition of aqueous 1N HCI (500 mL). The mixture was allowed to warm to rt and was extracted EtOAc (3 x 250 mL). Combined organic layer was dried over MgS04, filtered, and concentrated to dryness to give 4-chloro-1-(4-fluoro-3-methoxy-phenyl)pentan-1-one (32.50 g; quantitative ; 47% LC/MS purity) as a yellow liquid, used in the next step without further purification.

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 103291-07-2.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Electric Literature of 111-95-5, A common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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.

Compound 6-3 (5.3 g, 17.4 mmol) was dissolved in 1,4-dioxane (60 mL), followed by addition of compound 5-1 (4.85 g, 36.5 mmol), and potassium carbonate (4.9 g, 34.8 mmol) was added under stirring in batches, followed by stirring the reaction overnight at 70 C., TLC monitoring showed that the starting material 6-3 was completely reacted. The solvent was removed under reduced pressure to obtain a concentrated residue. The concentrated residue was dispensed with dichloromethane (20 mL), an appropriate amount of silica gel was added and the sample was stirred, spin-dried under reduced pressure and directly placed on a silica gel column for column chromatographic purification, with an eluent (dichloromethane:methanol=20/1-5/1) to obtain the target product 10-1 (2.2 g, 47.7%) as a pale yellow oil, LC-MS: m/z=266[M+H]+.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen China Resources Gosun Pharmaceutical Co., Ltd.; Jiang, Xiongjie; Huang, Quanhua; Yang, Zhanao; (43 pag.)US2017/2028; (2017); A1;,
Ether – Wikipedia,
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