Category: ethers-buliding-blocks

Electric Literature of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

1-114 80 mg (0.30 mmol) of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide 48 mul (0.36 mmol) of 2-phenyloxyethylamine 73 mg (0.33 mmol) of silver carbonate Ethanol 50¡ãC, 3.5h E 52

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

Reference:
Patent; Meiji Seika Pharma Co., Ltd.; Mitomi, Masaaki; Horikoshi, Ryo; Onozaki, Yasumichi; Nakamura, Satoshi; Nomura, Masahiro; Matsumura, Makoto; EP2633756; (2013); A1;,
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. 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Methoxy-4-(trifluoromethoxy)benzene

PREPARATION 34 2-Methoxy-5-trifluoromethoxybenzoyl chloride Combine 2-methoxy-5-trifluoromethoxybenzene (1.0 g, 5.2 mmol) and trifluoroacetic acid (200 mL). Add slowly portionwise hexamethylenetetraamine (26 g, 185.7 mmol). Heat at 60 C. After 24 hours, cool to ambient temperature and pour the reaction mixture into a 2 M aqueous solution of sulfuric acid (500 mL). Cool and extract ten times with diethyl ether. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding with 1/4 ethyl acetate/hexane to give 2-methoxy-5-trifluoromethoxybenzaldehyde.

The synthetic route of 710-18-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6423704; (2002); B1;; ; Patent; Aventis Pharmaceuticals Inc.; US6211199; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 22483-09-6, These common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, 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.

(4-Bromo-benzyl)-(2,2-dimethoxy-ethyl)-amine (1); 50 g (270.2 mmol) 4-bromobenzaldehyde were dissolved in 200 ml toluene and 28.4 g (270.2 mmol) aminoacetaldehyde dimethylacetal were added. After the addition of 5.1 g (27.0 mmol) p-toluenesulfonic acid monohydrate, the reaction mixture was heated under reflux in a Dean Stark apparatus. After 4 h, the reaction was cooled to room temperature and washed with saturated NaHCO3-solution (2x) and H2O. The combined aqueous layers were extracted with toluene and the combined organic layers were dried with MgSO4 and evaporated. The residue was dissolved in 200 ml ethanol and 5.11 g (135.1 mmol) sodium borohydride were added in small portions. After stirring for 2 h at room temperature and standing overnight, 5.0 ml acetic acid were added and the solvent was removed i. vac. The residue was taken up in dichloromethane and washed (2x) with H2O. After drying with MgSO4 and evaporation, 60.5 g of the title compound were obtained (crude product), which were used without further purification. Rt = 0.80 min (Method C). Detected mass: 274.1/276.1 (M+H+).

Statistics shows that 2,2-Dimethoxyethanamine is playing an increasingly important role. we look forward to future research findings about 22483-09-6.

Reference:
Patent; SANOFI-AVENTIS; WO2008/77553; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (4-Phenoxyphenyl)methanamine

EXAMPLE 4 N-isoquinolin-5-yl-N’-(4-phenoxybenzyl)urea The title compound was prepared using 4-phenoxybenzylamine, DBU, the product from Example 1A and the procedure described in Example 1B. 1H NMR(300MHz, d6-DMSO) delta 9.30 (s, 1H), 8.75 (s, 1H), 8.58 (d, 1H), 8.31 (d, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.60 (t, 1H), 7.40 (m, 4H), 7.18-6.95 (m, 6H), 4.38 (d, 2H); MS (DCI/NH3) m/z 369 (M+H)+.

The synthetic route of 107622-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2003/158188; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: (3-Bromopropoxy)benzene

Maslinic acid (MA) (150 mg, 0.3 mmol) was dissolved in dry DMF (5 mL), and finely grounded potassium carbonate (200 mg, 1.45 mmol) was added. After 60 min of stirring at 25 ¡ãC, (3-bromopropoxy)-benzene (150 mg, 0.7 mmol) was added, and stirring was continued for another 18 h. The mixture was poured into ice cold hydrochloride acid (5percent, 50 mL), and the white precipitate was filtered off. Chromatographic purification (silica gel, hexane/ethyl acetate, 7:3) followed by recrystallization (ethanol) gave the product; yield: 150 mg, 83percent; m.p. 166?170 ¡ãC; RF = 0.4 (n-hexane/ethyl acetate, 1:1); [alpha]D = +45.8¡ã (c 0.33, CHCl3); IR (KBr): nu = 3424vs, 2946vs, 2930vs, 2878m, 2864m, 1726vs, 1602m, 1498m, 1470s, 1458m, 1384s, 1364m, 1242s, 1202m, 1180m, 1172m, 1162s, 1124m, 1080m, 1052s, 1034m cm?1; 1H NMR (400 MHz, CDCl3): delta = 7.30?7.24 (m, 2H, CHaromat), 6.94 (dd, J = 7.3, 7.3 Hz, 1H, CHaromat), 6.88 (d, J = 8.0 Hz, 2H, CHaromat), 5.25 (dd, J = 3.4, 3.4 Hz, 1H, CH (12)), 4.27?4.14 (m, 2H, CH2 (31)), 4.03 (ddd, J = 6.1, 6.1, 1.5 Hz, 1H, CH2 (33)), 3.68 (ddd, J = 11.5, 9.7, 4.4 Hz, 1H, CH (2)), 2.99 (d, J = 9.5 Hz, 1H, CH (3)), 2.87 (dd, J = 13.8, 3.8 Hz, 1H, CH (18)), 2.18 (brs, 2H, OH), 2.15?2.06 (m, 2H, CH2 (32)), 2.00?1.86 (m, 2H, CHa (16) + CHa (1)), 1.83 (dd, J = 8.8, 3.4 Hz, 2H, CH2 (11)), 1.75?1.66 (ddd, J = 13.8, 13.8, 4.4 Hz, 1H, CHa (7)), 1.67?1.58 (m, 3H, CHa (19) + CHa (15) + CHb (16)), 1.57 (m, 1H, CH (9)), 1.54?1.45 (m, 2H, CHa (22) + CHa (6)), 1.43?1.35 (m, 1H, CHb (7)), 1.33?1.23 (m, 2H, CHa (21) + CHb (6)), 1.22?1.14 (m, 3H, CHb (19) + CHb (21) + CHb (22)), 1.11 (s, 3H, CH3 (27)), 1.02 (s, 3H, CH3 (23)), 1.05?0.95 (m, 1H, CHb (15)), 0.92 (s, 3H, CH3 (25)), 0.90 (s, 3H, CH3 (30)), 0.89 (s, 3H, CH3 (29)), 0.88?0.80 (m, 1H, CHb (1)), 0.81 (s, 3H, CH3 (24)), 0.80 (m, 1H, CH (5)), 0.66 (s, 3H, CH3 (26)) ppm; 13C NMR (100 Hz, CDCl3): delta = 177.8 (C=O, C28), 158.9 (Caromat, C34), 144.0 (C=CH, C13), 129.6 (CHaromat, C35), 122.4 (CH=C, C12), 120.9 (CHaromat, C36), 114.5 (CHaromat, C37), 84.1 (CHOH, C3), 69.1 (CHOH, C2), 64.3 (CH2, C31), 61.1 (CH2, C33), 55.4 (CH, C5), 47.7 (CH, C9), 46.9 (Cquart, C17), 46.5 (CH2, C1), 46.0 (CH2, C19), 41.9 (Cquart, C14), 41.4 (CH, C18), 39.5 (Cquart, C8), 39.3 (Cquart, C4), 38.4 (Cquart, C10), 34.0 (CH2, C21), 33.2 (CH3, C30), 32.7 (CH2, C7), 32.6 (CH2, C22), 30.9 (Cquart, C20), 28.8 (CH2, C32), 28.8 (CH3, C23), 27.7 (CH2, C15), 26.1 (CH3, C27), 23.8 (CH3, C29), 23.6 (CH2, C11), 23.1 (CH2, C16), 18.5 (CH2, C6), 17.1 (CH3, C26), 16.9 (CH3, C24), 16.7 (CH3, C25) ppm; MS (ESI, MeOH, source CID): m/z = 607.3 (20percent, [M + H]+), 629.3 (100percent, [M + Na]+), 929.3 (60percent, [3M + K + H]2+); analysis for C39H58O5 (606.87): C 77.18, H 9.63; found C 77.03, H 9.71.

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 588-63-6.

Reference:
Article; Siewert, Bianka; Csuk, Rene; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 1 – 6;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 2398-37-0,Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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.

General procedure: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 ¡Á 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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 RBF was charged with 1-bromo-3-fluoro-5-methoxybenzene (2.104 g, 10.26 mmol), (3-chlorophenyl)boronic acid (1.765 g, 11.29 mmol), potassium carbonate (4.25 g, 30.8 mmol), and Pd(Ph3P)4 (0.593 g, 0.513 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (25.7 ml) and water (8.55 ml) were added. A reflux condenser was attached, and the flask was lowered into a 90 C. heating bath for 45 min. The mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2*). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel column, 0-5% EtOAc/Heptane) to give 3′-chloro-3-fluoro-5-methoxy-1,1′-biphenyl (2.47 g, 10.44 mmol, 102% yield) as a clear oil containing about 10 wt % impurities.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 115144-40-6, name is 3,4-Difluoroanisole, A new synthetic method of this compound is introduced below., Computed Properties of C7H6F2O

Preparation 4 1-FL UORO-4-METHOXV-2-METHYLSULFANYL-BENZENE 1, 2-Difluoro-4-methoxy-benzene (100mg, 0. 69MMOL) and sodium methanethiolate (148mg, 2. 08MMOL) were dissolved in N, N-DIMETHYLFORMAMIDE (2mL) and the reaction mixture stirred at 60C for 18 hours. Additional sodium methanethiolate (99mg, 139MMOL) was added and the reaction mixture heated to 100C for 18 hours. The reaction mixture was diluted with water and extracted with ether (x 2). The ether extracts were washed with water (x 2), dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in pentane: ether 1: 1 mixture (2mL) and filtered through a plug of silica in a pipette, washing through with pentane: ether 1: 1 mixture (5mL). The reaction mixture was concentrated in vacuo to yield the title product as a colourless oil, 135mg. 1HNMR (CDCI3, 300MHZ) : 2.45 (s, 3H), 3.80 (s, 3H), 6.65 (dd, 1H), 6.80 (dd, 1H), 6.95 (t, 1H).

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; PFIZER LIMITED; PFIZER INC.; WO2005/9965; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 16618-68-1, 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 16618-68-1 as follows.

4.1.2. Synthesis of 5-hydroxy-7-bromo-quinoline from Scheme 2[0119]The title compound can be purchased by Shanghai Haoyuan Chemexpress Co., Ltd. CHINA or synthesized via known 3-bromo-5-methoxyaniline (Liedholm, Brita. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1984), B38(10), 877-84 or Hodgson, H. H.; Wignall, J. S Journal of the Chemical Society (1926)) in two steps. 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46 g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150??? C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through SiO2 and evaporation of solvent 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5 g, 74%) This mixture was separated to individual 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3:1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, molecular formula is C15H23BrO, 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. name: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

Reference Example 3 Bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide Under argon atmosphere, a solution of magnesium (4.0 g, 0.95 equivalents) and a small amount of iodine in THF (50 mL) was stirred at room temperature for 1 hour. After 4-bromo-2,6-di-tert-butylanisole (52 g, 0.175 mol) synthesised in Reference Example 2 was added at 46C to 53C thereto, the mixture was stirred at 5C for 1 hour. Then, dimethyl phosphite (11.4 g, 0.52 equivalents) was added and the mixture was stirred at 5C for 1 hour. After water (50 mL) was added at 3C and toluene (50 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An organic layer was washed successively with water (20 mL), a 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to obtain the title compound (11.6 g, pale yellowish white crystal). Yield 20.5%, mp. 166.1C. 1H-NMR (300 MHz, CDCl3, TMS) delta: 1.38 (s, 36H), 3.68 (s, 6H) 7.49 (s, 2H), 7.54 (s, 2H), 8.01 (d, 1H, J = 474.4 Hz).31P-NMR (121 MHz, CDCl3, 85%H3PO4) delta: 23.57 (dquint, J=474.1 Hz, 14.0 Hz). Elementary analysis for C30H47O3P Calculated value; C: 74.04, H: 9.73, P: 6.36 Found value; C: 74.13, H: 9.93, P: 6.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1516-96-7, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1568701; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem