Ethers-buliding-blocks

Some common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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: 32338-02-6

Under inert gas protection, 100 ml of a mixed organic solvent of acetic acid and acetonitrile with a volume ratio of 2: 1 was added to the reactorAgent, 10mmol successively added thereto the above formula (I-1) compound of the formula 12mmol (II-1) compounds, 1 mmol of copper trifluoromethanesulfonate catalyst, 1 mmol of cocatalyst, 20mmol bis (trifluoroacetate) iodobenzene, and To the reaction solution was added 15 mmol of isoamyl nitrite. The temperature was raised to 50 ¡ã C with stirring, and the reaction was stirred at this temperature for 8 hours. After the reaction was completed, all volatiles were removed in vacuo and the product extracted with ethyl acetate, the organic solvent phase was removed and the resulting residue was separated by column chromatography on 300-400 mesh silica gel, elution solvent is a volume ratio of 4: 1 petroleum ether and acetic acid Ethyl ester, the compound of the above formula (III-1) was obtained in a yield of 93.5percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32338-02-6, its application will become more common.

Reference:
Patent; Zhou Xiaofang; (6 pag.)CN107056703; (2017); A;,
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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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H16O4

Another exemplary study was carried out as follow: Compound J and AcOH (7.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C . Tetramethoxypropane (1.01 equivalents) was charged to the reactor and the j acket was set to maintain an internal temperature of 95 C. Once at temperature, the reaction continued mixing for 1.5 hours and then an IPC sample was taken. The passing criteria for this IPC was 60 C to prevent premature precipitation. Once the target volume was reached the jacket was set to maintain an internal temperature of 50 C. A 4 M solution of NaOH was then charged to the reactor via cannula to neutralize the remaining AcOH. This typically required approximately 10 volumes of the base solution. The neutralization was monitored by pH probe. Solids began to precipitate during the course of the charge. Once neutralized, the slurry was cooled to 20 C and held at that temperature for 1 hour prior to isolation via Buchner funnel. The cake was washed twice with 2 volumes of water and once with 2 volumes of MeOH. The solids were then dried to constant weight in a vacuum oven to provide Compound H. This procedure had been performed on 110 g scale to produce a granular light brown solid.

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
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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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-2-methoxynaphthalene

1-Bromo-2-methoxynaphthalene (20.0 g, 84.4 mmol),Phenylboronic acid (11.3 g, 92.8 mmol),Palladium acetate (0.10 g, 0.46 mmol),Triphenylphosphine (0.85 g, 2.78 mmol)And potassium phosphate (40.9 g, 177.9 mmol) were placed in a flask,Add 60 ml of water and 120 ml of dimethoxyethane mixed solution and reflux for 6 hours. After cooling at room temperature,Ammonium chloride aqueous solution (150 mL)And 200 mL of diethyl ether were injected,The organic layer was separated and the residue was extracted with diethyl ether,After drying the collected organic layer with magnesium sulfate,After removal of volatiles,The residue was purified with hexane using a silica gel chromatography tube,13.0 g (yield: 66%) of 2-methoxy-1-phenylnaphthalene as a colorless liquid was obtained.

The synthetic route of 3401-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK INNOVATION COMPANY LIMITED; OK, MYUNGAHN; SHIN, DONGCHEOL; JEONG, JISU; HAHN, JONGSOK; LEE, HOSEONG; SHIN, DAEHO; (23 pag.)JP5656843; (2015); B2;,
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Electric Literature of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.67 g (5 mmol) 4-[({[(1R, 2S, 4R)-1, 7, 7-TRIMETHYLBICYCLO [2.2. 1] hept-2-yl] amino} carbonyl)- AMINO]-LH-PYRROL-2-CARBONSUREETHYLESTER (Beispiel 1) werden IN 10 ml absolutem DMF gelst und mit 1.07 g (9.5 mmol) Kalium-tert-butylat versetzt. Nach 5 min Rhren bei RT werden 1.91 g (9.5 mmol) 1-BROMETHYL-2-PHENYLETHER zugegeben. Die Reaktionsmischung wird ber Nacht bei RT gerhrt, dann werden noch einmal 600 mg (3 mmol) 1-BROMETHYL-2-PHENYLETHER und 336 mg (3mmol) KALIUM-TERT-BUTYLAT zugegeben. Die Reaktionsmischung wird ber Nacht bei RT gerhrt, dann werden langsam 3.5 ml Wasser und 0.5 ml Methanol zugetropft. Die entstehenden Kristalle werden abgesaugt und mit Wasser/Methanol (1 : 1-Gemisch) und wenig Methanol gewaschen. Ausbeute : 1. 87 g (83 percent d. Th.) MS (ESI+) : m/z = 454 (M+H) + 1H-NMR (300MHZ, DMSO-d6) : deltaelta; = 7.9 (s, 1H), 7.25 (TR, 2H), 7.2 (d, lH), 6.85-6. 95 (m, 3H), 6.65 (d, 1H), 6.0 (d, 1H), 4.6 (TR, 2H), 4.15-4. 25 (m, 4H), 3.95 (m, 1H), 2.2 (M, 1H), 1.55-1. 8 (m, 3H), 1.35-1. 1 (m, 2H), 1.25 (tr, 3H), 0.9 (s, 3H), 0.85 (s, 3H), 0.8 (D, 1H), 0.75 (s, 3H) ppm.

The synthetic route of ((2-Bromoethoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/52852; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 202865-59-6, name is 2-Bromo-4,6-difluoroanisole, 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 202865-59-6, Application In Synthesis of 2-Bromo-4,6-difluoroanisole

[00190] Intermediate 18A. l-(3,5-Difluoro-2-methoxyphenyl)-2- (diphenylmethylene)hydrazine: To a mixture of palladium (II) acetate (0.040 g, 0.18 mmol) and xantphos (0.104 g, 0.179 mmol) in toluene (1 mL), l-bromo-3,5-difluoro-2- methoxybenzene (4.0 g, 18 mmol), (diphenylmethylene)hydrazine (3.52 g, 17.9 mmol) and sodium tert-butoxide (2.41 g, 25.1 mmol) were added followed by the addition of toluene (4 mL). The mixture was degassed twice and stirred for 6 h at 100 C under argon. After cooling to room temperature, EtO Ac and water were added. The organic layer was separated. The aqueous layer was extracted one more time with EtOAc. The combined organics were washed with water and brine, dried over MgSC^, filtered, and concentrated. The crude was purified by flash chromatography, eluting with EtOAc/hexanes to give Intermediate 18A (6.0 g, 84% yield). LCMS (ESI) m/z 339.4 (M+H)+, RT = 2.33 min (Method D). NMR (400 MHz, CDC13) delta ppm 3.63 (br. s, 3 H), 6.14 – 6.38 (m, 1 H), 7.08 – 7.20 (m, 5 H), 7.45 – 7.68 (m, 5 H), 7.97 (s, 1 H). 19F NMR (376.5 MHz, acetone-d6) delta ppm -115.46, -129.88.

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, 2-Bromo-4,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); 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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H20O3

General procedure: Triethyl orthoformate, orthoacetate, orthopropionate or orthobenzoate(10 mmol) was added dropwise to the mixture of 1,2,4,5-tetrazine-3,6-dicarbohydrazide (6) (0.5 g, 2.5 mmol), Lawesson’s reagent(1.12 g, (2.77 mmol) and glacial acetic acid (7 mL). The reaction wascarried out using conventional heating or microwave irradiation(150 W) in five cycles of 90 s with 2 min intervals at the temperature50-100 C.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; K?dzia, Anna; Kudelko, Agnieszka; ?wi?tkowski, Marcin; Kruszy?ski, Rafa?; Dyes and Pigments; vol. 172; (2020);,
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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 116557-46-1 as follows. category: ethers-buliding-blocks

(E)-N-(3-Bromo-2-methoxyphenyl)-3-ethoxyacrylamide (3c); A mixture of 3-bromo-o-anisidine (2c) (4.50 g, 22.3 mmoles) and pyridine (15 mL) was placed in an icebath. (E)-3-ethoxy-2-propenoyl chloride (1) (3.75 g, 27.9 mmol) was added dropwise as the solution stirred continuously for one hour. The mixture was concentrated to remove the pyridine and was transferred to a seperatory funnel where AcOEt and water were added. Concentrated HCl was added until the aqueous layer was pH 1. The water layer was extracted twice with AcOEt and the organic layers were washed with saturated NaCl (25 mL) containing 1 M HCl (2 mL). The procedure was followed by a second wash of saturated NaCl (25 mL) containing saturated NaHCO3 (5 mL). The organic layer was finally washed with saturated NaCl (25 mL). The product layer was dried and filtered through silica gel (2) using a solvent system of 1:1 followed by 2:1 hexanes-AcOEt. The product was chromatographed (2:1 1:1 hexanes:AcOEt) and recrystalized from 10:1 hexanes-AcOEt to afford light brown-orange crystals (3.35 g, 50% yield): mp 102-104 C; 1H NMR (400 MHz, CDCl3) 8.35 (dd, J=8.4, 1.6 Hz, 1H), 7.65 (d, J=12.4 Hz, 1H), 7.52 (bs, 1H), 7.21 (dd, J=8.4, 1.6 Hz, 1H), 6.98 (t, J=8.4 Hz, 1H), 5.36 (d, J=12.0 Hz, 1H), 3.97 (q, J=7.2 Hz, 2H), 3.86 (s, 3H), 1.37 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 116557-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Horwitz, Jerome P.; Polin, Lisa; US2007/60612; (2007); A1;,
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Related Products of 888327-32-0, 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. 888327-32-0, name is 4-Bromo-1-(difluoromethoxy)-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: ((4-(Difluoromethoxy)-3-methylphenyl)ethvnyl)trimethylsilane; In a 250 mL round-bottomed flask was placed 4-bromo-1-(difluoromethoxy)-2- methylbenzene (14 g, 59.1 mmol) from the previous step. Pyrrolidine (23.6 mL) and acetonitrile (35.4 mL) were added to give a colorless solution. The reaction was degassed by bubbling with N2. Ethynyltrimethylsilane (7.0 g, 10 mL, 70.9 mmol) was added followed by bis(triphenylphosphine)dichloropalladium (2.07 g, 2.95 mmol) and copper(l) iodide (0.56 g, 2.95 mmol) was added. The reaction was warmed to 65 0C for 4h. The reaction was cooled. The solution was partitioned between EtOAc (200 mL) and 1 M HCI (200 ml_). The organic was washed with 1M HCI (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4 and filtered. The solvent was removed and the resulting crude material was purified by flash chromatography (SiO2, 100% hexanes) to provide 12.4 g, 83%, of the title compound as a light yellow oil.

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

Reference:
Patent; WYETH; WO2008/115552; (2008); A1;,
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Application of 332-48-9, 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 116 1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride STR152 From a mixture of 4-(4-methylbenzyl)piperidine (500 mg, 2.21 mmol), 2-(4-fluorophenoxy)ethyl bromide (508 mg, 2.32 mmol) and K2 CO3 (626 mg, 4.53 mmol) in CH3 CN (20 mL) was obtained the title compound as colorless plates (293 mg, 63%), mp 189-191 C., 1 H NMR (CDCl3) 1.60-2.12 (m, 5H), 2.31 (s, 3H), 2.57 (d, J=7.2 Hz, 2H), 2.62-2.82 (m, 2H), 3.20-3.55 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-6.84 (m, 2H), 6.92-7.02 (m, 6H), 7.08 (d, J=8.1 Hz, 2H), 12.56 (bs, 1H); Anal. Calcd for C21 H27 ClFNO: C, 69.31; H, 7.48; N, 3.85. Found: C, 69.49; H, 7.39; N, 3.88.

The synthetic route of 1-(2-Bromoethoxy)-4-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 solution of (S*)-3-methyl-7-(methylcarbamoyl)-3-phenyl-2,3-dihydrobenzofuran-5-carboxylic acid (100 mg, 0.321 mmol) in DMF (1 ml.) was added sequentially HATU (183 mg, 0.482 mmol) and DIPEA (0.140 ml_, 0.803 mmol). The reaction was stirred for 1 min then 3,3-diethoxypropan-l-amine (0.057 ml_, 0.35 mmol) was added. The reaction was stirred for 1 h. Sat. LiCI (aq) and EtOAc were added and the layers separated. The aqueous layer was extracted with further EtOAc and the organic layers were combined, back extracted with sat. LiCI (aq) and water and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo to give a dark oil. This oil was purified using silica gel column chromatography eluting with a gradient of 60-100% EtOAc : cyclohexane and the appropriate fractions collected and concentrated in vacuoto afford (S*)-N5-(3,3-diethoxypropyl)-N5′,3-dimethyl-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxamide (141 mg, 0.320 mmol, 100 % yield) as a yellow solid LCMS (method Formic): Retention time 1.08, [M+H]” = poor ionisation

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LUCAS, Simon Christopher Cranko; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (89 pag.)WO2019/68782; (2019); A1;,
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