Category: ethers-buliding-blocks

Reference of 2688-84-8,Some common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, molecular formula is C12H11NO, 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 solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40% hydrobromic acid (50 ml) at 0 C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40% hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5% hydrochloric acid, 10% potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45%) was obtained by column purification of the crude intermediate using pet ether as eluent

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

Reference:
Patent; ASTRAZENECA AB; US2008/15237; (2008); A1;,
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Synthetic Route of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Synthesis of 1-(4-methoxy-2-methylphenyl)propan-2-one (C8) Four batches of this experiment were carried out (4*250 g substrate). Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-yl acetate (187 g, 1.87 mol), palladium(II) acetate (7.5 g, 33 mmol) and tris(2-methylphenyl)phosphane (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 C. for 18 hours. After cooling to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 C. The resulting mixture was diluted with toluene (500 mL) and filtered through Celite; the filter pad was thoroughly washed with ethyl acetate (2*1.5 L). The organic phase from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield: 602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 7.05 (d, J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (s, 3H), 3.65 (s, 2H), 2.22 (s, 3H), 2.14 (s, 3H).

The synthetic route of 1-Bromo-4-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
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Related Products of 588-63-6, 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.

Scheme IV, Step S: Synthesis of 1-(3-phenoxy-propyl)-piperidine (Scheme IV, Compound 4) Mix 3-phenoxypropyl bromide (801.5 g, 3.73 mol), potassium iodide (61.8 g, 0.37 mol, 0.10 equivalents) and water (4.0 L) in a 12-L, 3-necked flask fitted with: a stirrer, thermometer in a side-arm adapter, connected to a Firestone.(R). valve and an addition funnel fitted with a gas outlet adapter, connected to a bubbler. Add piperidine (634.6 g, 7.45 mol, 2.0 equivalents) over 1 hour, without cooling under nitrogen. The temperature at the end of the addition is 40°C. Heat the reaction mixture and maintain the temperature at 50°C for 6 hours. Monitor the progress of the reaction by HPLC (Column=300 x 3.9 mm Phenomenex Bondclone 10 CN; mobile phase=65percent acetonitrile:35percent 0.1N ammonium formate buffer; flow=1.5 mUminute; wavelength=215 nm; RT: 3-phenoxypropyl bromide=2.3 minutes; 37=4.4 minutes). Typically, the conversion is 94percent. Cool the reaction mixture to ambient temperature over a time period of 14 hours and extract with dichloromethane (2 x 4.0 L). Combine the organic extracts and dry over MgSO4 (400 g). Filter off the drying agent and wash with dichloromethane (1.0 L). Concentrate the filtrate (35-40 °C/50 torr) to give 800 g, 98percent Yield) of 4, as an oil. HPLC analysis shows that 37 is 90percent pure. Purify 4 (16.5 g portion) by distillation under vacuum and collect the title compound (10 g) as a colorless liquid at 99-105°C/0.3 mm: 1H NMR (CDCl3, 200MHz) delta 1.38-1.5 (m, 2H), 1.5-1.64 (m, 4H), 1.9-2.1 (m, 6H), 4.0 (t, 2H), 6.85-6.95 (m. 3H), 7.22-7.3 (t, 2H). Analysis calculated for C14H21NO: C, 76.67; H, 9.65; 6.39. Found: C, 76.55; H, 9.50; N, 6.22. [M+H]+=220 m/e.

The chemical industry reduces the impact on the environment during synthesis (3-Bromopropoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharmaceuticals Inc.; EP1216244; (2003); B1;,
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These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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. Safety of 2-Phenoxyethylamine

General procedure: A 10mL microwave vial was charged with 4 or 5 or 6 (1.0 mmol), a small excess (1.2 mmol) of 2-phenoxy- or (2-methoxyphenoxy)-or (2,6-dimethoxyphenoxy)-ethanamine and a catalytic amount ofpotassium iodide in 1 mL of 2-methoxyethanol. The reaction wasstirred under microwave irradiation at 160 °C (pressure 100 PSI, power 50 W) for 30 min. Then the solvent was evaporated under reduced pressure. The residue was taken up with EtOAc, basified with 5percent NaOH. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography.

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

Reference:
Article; Franchini, Silvia; Manasieva, Leda Ivanova; Sorbi, Claudia; Battisti, Umberto M.; Fossa, Paola; Cichero, Elena; Denora, Nunzio; Iacobazzi, Rosa Maria; Cilia, Antonio; Pirona, Lorenza; Ronsisvalle, Simone; Arico, Giuseppina; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 435 – 452;,
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1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, 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. HPLC of Formula: C9H12O2

General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun; Heterocycles; vol. 94; 1; (2017); p. 86 – 94;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester: To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150° C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Yihan; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Bohacek, Regine; US2003/100573; (2003); A1;,
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Electric Literature of 6298-96-0, These common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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 suspension of tert-butyl 4-(2-(6-methoxypyridin-3-yl)-2-oxoethyl)piperidine-1 -carboxylate (3.00 g, 8.97 mmol) and (S)-1 -(4-methoxyphenyl)ethan-1 -amine (2.00 mL, 13.5 mmol) in titanium(IV) isopropoxide (7.89 mL, 26.9 mmol) was stirred at 90 C. The reaction progress was monitored by LCMS (aliquots treated with MeOH, NaBH4, followed by 1 N HCI). LCMS indicated complete reaction after 1 hour. The yellow solution was cooled to 0 C, diluted with MeOH (15 mL), treated slowly with NaBH4 (0.509 g, 13.46 mmol) in portions. After 1 hour, the solution was warmed to RT and stirred for an additional 4 hours.. The reaction was quenched with saturated aqueous NH4CI and 1 N HCI and then extracted with EtOAc. The EtOAc solution was washed with saturated aqueous NaHC03, brine, dried over Na2S04, filtered, and concentrated. 1H-NMR analysis of the crude material showed an approximately 2:1 mixture of SS : RS diastereomers. Purification by flash chromatography (silica gel, 0-100% EtOAc/hexanes, gradient elution) afforded tert- butyl 4-((S)-2-(((S)-1 -(4-methoxyphenyl)ethyl)amino)-2-(6-methoxypyridin-3- yl)ethyl)piperidine-1 -carboxylate (2.39 g, 57% yield) as clear oil. LCMS (ESI) m/z calcd for C27H39N3O4: 469.3. Found: 470.4 (M+1)+. NMR (400MHz, CDCI3) delta 7.85 (s, 1H), 7.48 (d, J = 8.6 Hz, 1H), 7.12 (d, J = 8.2 Hz, 2H), 6.87 (d, J = 8.2 Hz, 2H), 6.76 (d, J = 8.6 Hz, 1H), 4.08 – 3.88 (m, 5H), 3.82 (s, 3H), 3.40 (q, J = 6.4 Hz, 1H), 3.33 (t, J = 6.6 Hz, 1H), 2.67 – 2.43 (m, 2H), 1.66 – 1.48 (m, 2H), 1.47 – 1.16 (m, 15H), 1.09 – 0.82 (m, 2H).

Statistics shows that 1-(4-Methoxyphenyl)ethylamine is playing an increasingly important role. we look forward to future research findings about 6298-96-0.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVINDAR, Ghotas; KAZMIERSKI, Wieslaw Mieczyslaw; MILLER, John Franklin; SAMANO, Vicente; SUWANDI, Lita; TEMELKOFF, David; WASHIO, Yoshiaki; XIA, Bing; (152 pag.)WO2019/3142; (2019); A1;,
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Reference of 588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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.

Example XII.1 (S)-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-carbamic acid tert-butyl ester 6.21 g (19.1 mmol) cesium carbonate are added to a mixture of 5.80 mg (19.1 mmol) (S)-[1-(4-piperidin-4-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester (V.5), 4.21 g (21.0 mmol) 1-bromo-4-ethoxy-benzene, 454 mg (0.953 mmol) X-Phos and 214 mg (0.953 mmol) palladium(II) acetate in 50 mL toluene/10 mL tert-butanol. The mixture is stirred for 3 h at 120 C. under inert gas atmosphere. After that time, the mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water and dried over magnesium sulphate. The solvent is removed in vacuo and the residue is recrystallized from acetonitrile. C26H36N2O3 (M=424.6 g/mol) ESI-MS: 425 [M+H]+

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
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Application of 3401-47-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3401-47-6 name is 1-Bromo-2-methoxynaphthalene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

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

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
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Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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. Recommanded Product: 1,4-Dimethoxy-2,3-dimethylbenzene

The compound 72 (5 g, 30.1 mmol) was dissolved in TFA (50 mL) and hexamine (4.7 g, 33.1 mmol) was added to the resulting solution. The reaction mixture was refluxed under dry conditions for 2 hours. The TFA was evaporated under reduced pressure and the residue was dissolved in EtOAc (100 mL) . and the The resulting organic solution was washed with water (3×50 mL) and then dried over Na2SO4. The solvent organic phase was evaporated concentrated in vacuum and the residue was subjected to silica gel column chromatography (petroleum ether/EtOAc 20: 1 to 10: 1) to giveproduct 73 (3.1 g, 53) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-83-5, its application will become more common.

Reference:
Patent; XW LABORATORIES, INC.; XW LABORATORIES INC.; XIANG, Jia-Ning; QI, Zude; NING, Dezheng; LIU, Xianbo; (152 pag.)WO2019/33330; (2019); A1;,
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