Month: September 2021

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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Synthesis of (S)-(-)-1-(4-hydroxyphenyl)ethylamine hydrobromide (6) A solution of (S)-(-)-1-(4-methoxyphenyl)ethylamine (5, 75 g, 496.7 mmol) in 30% hydrogen bromide in acetic acid (350 mL, Aldrich) in a 1 liter sealed tube was heated at 100-110 C. in an oil bath for 6 hours. The reaction was cooled to room temperature, and nitrogen gas was bubbled into the solution to purge the excess HBr (the HBr was purged into aqueous NaOH). Volatiles were then removed in vacuo to afford the crude phenol amine HBr salt 9 (110 g) as a brown oil, which was used in the next reaction without further purification.

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; Bristol-Myers Squibb Company; US2008/9534; (2008); A1;,
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Electric Literature of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-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.

(0677) 4-Bromo-2-methoxyaniline (6.8 g, 33.7 mmol) and di-tert-butyl dicarbonate (8.9 g, 40.8 mmol) were dissolved in tetrahydrofuran (100 mL). Under the protection of nitrogen gas, the reaction was carried out under reflux for 22 h, and the mixture was cooled. The solvent was removed by distillation under reduced pressure, and ethyl acetate (150 mL) was added. The mixture was washed with 1 mol/L hydrochloric acid, and the water phase and the organic phase were separated. The organic phase was dried with anhydrous sodium sulfate, and filtrated under suction. The filtrate was concentrated to get the title compound (8.3 g, yield: 81.6%).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2944-49-2, name is 1-Methoxy-2,3-dimethylbenzene, 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 2944-49-2, HPLC of Formula: C9H12O

A mixture of 2,3-dimethylanisole (50g, 0.37 mol), CU2, 1 sulfate pentahydrate (90 g, 0.36 mol), and potassium peroxydisulfate (301 g, 1.11 mol) in acetonitrile/water (1: 1,2. 6 L) was stirred vigorously and heated to reflux for 30 minutes. Thin layer chromatography (Hexane: EtOAc, 8: 2) showed no starting material and one new spot. The reaction was cooled to room temperature and extracted with CH2CL2 (4L) and washed with water (2L). The layers were separated and the aqueous layer was again extracted with CH2CL2. The organic layers were combined and concentrated, 55 g obtained (-100%), product was taken on as is. H-NMR (DMSO-D6) : 10.05 (s, 1H), 7.78 (m, 1H), 6.95 (m, 1H), 6.88 (s, 1H), 3.84 (s, 3H), 2.6 (s, 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, 1-Methoxy-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63155; (2004); A1;,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, A new synthetic method of this compound is introduced below., SDS of cas: 53087-13-1

A solution of 1-(benzyloxy)-3-bromobenzene (for a preparation see Intermediate 21 , 263 mg, 1.0 mmol) in 1 ,4-dioxane (8 mL) was added to a mixture of £>/s(pinacolato)diboron (1 .27 g, 5.0 mmol), potassium acetate (392 mg, 4.0 mmol) and [1 ,1 – t)/’s(diphenylphosphino)ferrocene]dichloropalladium(ll), (PdCI2(dppf)) (37 mg, 5 mol%). The reaction mixture was heated in a microwave at 1 10C for 60 minutes. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and filtered through Celite. The filtrate was dried and evaporated to give 2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (310 mg, 1.000 mmol, 100 in the next step without further

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
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Synthetic Route of 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.

Add NaH (0.47 g, 11.8 mmol) to a solution of morpholin-3-one (Vieles, P.; Seguin, J., Bulletin de Ia Societe Chimique de France, 1953, 287-9) (1.0 g, 9.9 mmol) in DMF (10 ml) at room temperature. Stir for 30 min, add (2-bromo-ethoxymethyl)-benzene (2.2 g, 10.2 mmol), and stir at room temperature for 18 h. Dilute with water and extract with EtOAc (2x). Combine the organics, dry, and concentrate. Purify by flash chromatography using 0 – 5% MeOH in CH2Cl2, to give the product as an oil. (1.7 g, 74%). 1H NMR (400 MHz, CDCl3): delta 7.28 (m, 5H), 4.48 (s, 2H), 4.13 (s, 2H), 3.80 (t, 2H, /=5.1 Hz), 3.65 (m, 2H), 3.59 (dd, 2H, 7=7.5, 2.6 Hz), 3.48 (t, 2H, J=5.1 Hz).

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; ELI LILLY AND COMPANY; WO2006/66174; (2006); A1;,
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Related Products of 168971-68-4, These common heterocyclic compound, 168971-68-4, name is 1-Bromo-2-fluoro-4-(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.

A mixture of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene Int-172-38 (12.8 g, 49.4 mmol), benzophenone imine (10 mL, 59.3 mmol), Pd2(dba)3 (1.1 g, 1.23 mmol), XantPhos (2.8 g, 4.9 mmol) and NaOtBu (5.7 g, 59.3 mmol) in 1,4-dioxane (100 mL) was stirred and heated at 100 C overnight. After cooling to room temperature, the mixture was concentrated. The residue was then partitioned between EtOAc and H2O, and the organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using hexanes/EtOAc (0 to 5% EtOAc in hexanes). The product was dissolved in THF (100 mL), and 1M aqueous HCl (50 mL) was added. After being stirred at room temperature for 1h, the mixture was partitioned between EtOAc and H2O. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes). The product 30 was obtained as pale brown oil in 30% yield (5.4 mg). LCMS: (M+1) m/z = 196.

Statistics shows that 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 168971-68-4.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BLACKTHORN THERAPEUTICS, INC.; ROBERTS, Edward; GUERRERO, Miguel A.; URBANO, Mariangela; ROSEN, Hugh; JONES, Rob; LAXAMANA, Candace Mae; ZHAO, Xianrui; TURTLE, Eric Douglas; (331 pag.)WO2018/170492; (2018); 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 19056-40-7 as follows. HPLC of Formula: C7H8BrNO

3-Methoxy-4-bromoaniline (10.0 g, 0.0494 mol) and dimethylacetylene dicarboxylate(7.46 g, 0.0525 mol) were combined in methanol (71 mL) and Dowtherm (140 mL) and refluxed under nitrogen for 18 hrs. The reaction was cooled and concentrated to give an oily residue and additional Dowtherm (20 mL) was added. This solution was added dropwise via syringe to Dowtherm (120 mL) at 250 0C and allowed to stir at 250 0C for an additional 15 min (precipitate observed). The reaction mixture was cooled to room temperature, solids filtered and washed with hexanes to give 14.4 g solid. EPO The solid was resuspended in dichloromethane (200 mL) and stirred for 30 min. The solid was filtered to give to give 34 (13.8 g, 90percent yield). LRMS (M+H)+ = 312.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/119061; (2006); A2;,
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Related Products of 588-63-6, These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: Maslinic acid (MA, 1equiv) was dissolved in dry DMF (5mL), and finely grounded potassium carbonate (5 equiv) was added. After 60min of stirring at room temperature, the corresponding alkyl or benzyl bromide (2equiv) was added, and stirring was continued for 18h. The mixture was poured into an ice cold aq. HCl (5percent, 50mL), and the white precipitate was filtered off. Chromatographic purification (silica gel, hexane/ethyl acetate, 7:3) and recrystallization (ethanol) afforded the product.

Statistics shows that (3-Bromopropoxy)benzene is playing an increasingly important role. we look forward to future research findings about 588-63-6.

Reference:
Article; Siewert, Bianka; Pianowski, Elke; Obernauer, Anja; Csuk, Rene?; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 594 – 615;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., name: ((3-Bromopropoxy)methyl)benzene

Compound 3F: 1 -[3-(Benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazoleA mixture of 4-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1 /-/-pyrazole (5.0 g, 26 mmol), potassium carbonate (4.27 g, 30.9 mmol) and 1-bromo-3-benzyloxypropane (6.20 g, 27.0 mmol) in DMF (20 mL) was stirred at 80 °C overnight, quenched with water (20 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (2 x 30 mL), brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ISCO system: EtOAc/Heptane = 30- 70percent) to afford 7.67 g of the title compound as a light-yellow oil (87percent). 1H NMR (CDCI3, 400 MHz): delta = 7.80 (s, 1 H), 7.66 (s, 1 H), 7.30-7.36 (m, 5H), 4.48 (s, 2H), 4.28 (t, J = 6.8 Hz, 2H), 3.43 (t, J = 5.8 Hz, 2H), 2.17 (m, 2H), 1.33 (s, 12H). MS (ES+): m/z = 343.36 [MH+]. HPLC: iR = 4.20 min ( ZQ3: polar_5 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
Ether – Wikipedia,
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38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 38336-04-8

(1) Take 5g of p-fluoronitrobenzene dissolved in 50ml of acetonitrile,5.72 g under ice bath2-benzyloxyethylamine (A) is added to the above solution,Then add 9.5 ml of triethylamine,Reaction at 50C for 8 hours,A yellow clear solution is obtained,The reaction solution was concentrated under reduced pressure,Dissolved in 200 ml of dichloromethaneWash 50 ml of water three timesThe organic phases are combined and dried over anhydrous sodium sulfate.After filtration, spin down to give a crude product.The crude product was purified by column chromatography to give intermediate II 4.5 g as a yellow oil.Yield 48.1%.

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; Li Yantao; Mao Yu; Zhang Chi; Liu Chun; Cui Xilin; (13 pag.)CN107586291; (2018); A;,
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