Category: ethers-buliding-blocks

588-96-5, name is p-Bromophenetole, 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. Computed Properties of C8H9BrO

5.0 g of 4-bromophenylethyl ether and 100 mL of anisole were mixed and stirred until clear. spare. Add 0.72g of magnesium turnings and 100mL of anisole in turn, stir and mix thoroughly, pour 20mL of 4-bromophenethyl ether anisole solution into it, heat up to 47 C, reach the specified temperature, stop stirring, add 0.63 g of elemental iodine particles initiated the reaction and there was bubble overflow at the bottom of the system. When a large amount of air bubbles overflow, start stirring and stir slowly until the system turns from deep red to colorless, clear and transparent, and the temperature of the system is significantly improved. After adding 0.63 g of elemental iodine particles, the normal rotation speed was resumed, and the remaining 4-bromophenylethyl ether anisole solution was started to be added dropwise, and the temperature of the system was maintained at a micro reflux state, and the dropwise addition was completed in 1.2 hours. After the completion of the dropwise addition, the micro reflux reaction was maintained for 2 hours. The heating was stopped, the temperature was lowered to 3 C, and 0.47 g of cuprous iodide was added to the reaction vessel, and the temperature was further lowered to -18 C.9.96 g of 2-(bromomethyl)-4-iodochlorobenzene was mixed in 100 mL of anisole for use.When step (3) reaches the specified temperature of -18 C, slowly add 2-(bromomethyl)-4-iodochlorobenzene in anisole solution, and there is obvious temperature rise process in the middle stage before the dropwise addition, control The reaction system was reacted at -18 C. The temperature increase during the late addition was not obvious, and the addition was completed in 2.2 hours. After the dropwise addition was completed, the mixture was stirred for 2 hours. The cooling was stopped, and the temperature was naturally raised to room temperature, and stirring was continued for 12 hours. The system was quenched with 1N aqueous HCl.Concentrate to a small volume until crystallized, filter, and filter cake washed with pure water and blast dried. Weighed to obtain the target product (the yield of the product 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene was 8.94 g, the purity was 99.5%, and the yield was 95.9%)

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

Reference:
Patent; Nanjing Hongshan Biological Technology Co., Ltd.; Wu Fahao; Li Gang; Gao Yangzhe; (8 pag.)CN109232199; (2019); A;,
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Synthetic Route of 18800-30-1,Some common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, molecular formula is C8H8Br2O, 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.

b) 52.0 g (186 mmol) of 1-bromo-4-(2-bromoethoxy)benzene is added to 300 ml THF and chilled to 0 C. Within 30 min 25.0 g (223 mmol) KOtBu are added to this mixture in several portions. The cooling bath is removed and the reaction mixture is stirred at r.t. over night. The reaction is queched by the addition of water. The resulting mixture is extracted with EtOAc (2¡Á). The org. phases are combined, washed with sat. aq. NaCl solution, dried with MgSO4 and the solvent is removed in vacuo. The resulting product is used without further purification.

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-4-(2-bromoethoxy)benzene, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/100211; (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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Step b: To a degassed (argon) solution of 3b (10.0 g, 49.7 [MMOL)] in DMF (310 mL) was added bis (pinacolato) diborane (13.9 g, 54.7 [MMOL), KOAC] (14.2 g, 149 [MMOL)] and [PDCL2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL).] The reaction mixture was heated to 80 C for 24 h then was cooled to 25 [C.] 4-Bromobenzeneacetic acid (21.4 g, 99.5 [MMOL),] aqueous 2 M [NA2CO3 SOLUTION] (124 mL, 248 [MMOL)] and additional [PDCI2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL)] were added to the mixture. The reaction mixture was heated to [80 C] for 12 h. The cooled mixture was acidified with aqueous 4 N HCI solution and extracted with EtOAc (3 x). The combined organic layers were successively washed with water (2 x) and brine, dried [(MGS04),] filtered and concentrated under reduced pressure. The crude resulting acid was dissolved in [ET2O] and was treated with excess ethereal [CH2N2] solution (ca. 0.6 M). The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc, 19/1) to give 3c (4.25 g, 32% yield) as a pale yellow solid.

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; BOEHRINGER INGELHEIM (CANADA) LTD.; WO2004/26875; (2004); A1;,
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Application of 1579-40-4, The chemical industry reduces the impact on the environment during synthesis 1579-40-4, name is Di-p-tolyl Ether, I believe this compound will play a more active role in future production and life.

Tolyl Ether (5.9 gm, 30 mmoles), bipheylcarboxylic acid (6 gm, 30.27 mmoles), zinc chloride (12 gm, 88 mmoles) and phosphorus oxychloride (20 mmoles) were stirred at 95 degree in an oil bath for 2 hrs. The mixture was cooled to room temperature and the viscous mixture is poured into cracked ice and stirred overnight. The solid was collected and washed with water. The solid was suspended in 150 ml of methanol and was heated to boiling for 5 min. The mixture was cooled to room temperature, filtered and dried to a constant weight (8.4 g, yield: 74%).

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, Di-p-tolyl Ether, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISIS PHARMACEUTICALS, INC.; WO2005/77966; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10541-78-3, name is 2-Methoxy-N-methylaniline, 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 10541-78-3, Quality Control of 2-Methoxy-N-methylaniline

This compound was obtained by reacting 2-methoxy-N-methylaniline (3.0 g, 21.9 mmol.) and cyclopentanone (9.20 g, 109mmol) in the presence of a catalytic amount of iodine (278 mg, 1.09 mmol).After purification on a silica gel column using hexanes-ethyl acetate (95: 5),compound 10a was obtained as a yellowish oil (2.35 g, 42%). 1H NMR (CDCl3, 400 MHz): delta 1.68-1.72(2H, m), 1.76-1.82 (2H, m), 1.85-1.92 (2H, m), 2.01-2.07 (2H, m), 2.51-2.56(2H, m),2.65-2.70 (2H, m), 4.05 (3H, s), 4.47 (1H, brs, NH), 5.01 (1H, m), 6.03(1H, m), 6.58 (1H, d, J = 7.6 Hz),6.60 (1H, d, J = 4.0 Hz), 6.65 (1H,dd, J = 7.6 and 4.0 Hz). 13CNMR (CDCl3, 100 MHz): delta 22.6, 24.1, 31.6, 32.4, 40.2, 55.8, 64.8,109.3, 115.9, 116.3, 120.5, 132.2, 132.3, 138.8, 145.4. EI-MS (GC-MS): m/z(5) 255 [M]+ (30), 227(100), 213(15)

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-Methoxy-N-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fotie, Jean; Ayer, Suraj K.; Poudel, Binit S.; Reid, Carolyn S.; Tetrahedron Letters; vol. 54; 51; (2013); p. 7069 – 7073;,
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Related Products of 910251-11-5, 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 910251-11-5 as follows.

To a solution of 208A (300mg, O.lmmol) and potassium trifluoro(methoxymethyl)borate (304mg, 0.2 mmol) in 3 ml dioxane/water (10:1) was added 3 aq. Cs2C03 and 2- dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (Ruphos)(93.4mg, 0.2 mmol) andPalladium(II)acetate (22.5 mg, 0.1 mmol). The resulting mixture was heated at reflux for overnight. The reaction mixture was filtered and the mixture was extracted with EtOAc. The organics were dried over Na2S04, filtered and concentrated. The crude product was purified by Si02 chromatography eluting with a gradient of EtOAc in hexanes to provide 12 mg of title compound. MS (m/z) 267 [M+H]+.

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 36865-41-5, Formula: C4H9BrO

To a suspension of Mg (911 mg, 37.5 mmol) and of iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of 1-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard formation had started. The rest of the 1-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard sol. (1M in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4-dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane?EtOAc/heptane 1:1) yielded the title compound (1.51 g, 62%). LC-MS: tR=0.80 min; ES+: 260.15.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-methoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2009/62342; (2009); 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 31804-36-1 as follows. category: ethers-buliding-blocks

(E)-ethyl 3-(3-methoxy-2-methylphenyl)acrylateTo a solution of 1-bromo-3-methoxy-2-methylbenzene (515 mg, 2.56 mmol) in DMF (10 ml_) at RT was added ethyl acrylate (2564 mg, 25.6 mmol) and N-ethyl-N- isopropylpropan-2-amine (2.68 ml_, 15.37 mmol), tri-o-tolylphosphine (312 mg, 1.025 mmol), Pd(OAc)2(1 15 mg, 0.512 mmol). The reaction mixture was heated in microwave under high absorption at 150 C for 2 h. The reaction mixture was passed through celite and washed with EtOAc. The filtrate was washed with water twice, brine (1x). The organic layer was collected and concentrated to give the crude product. The crude product was purified on a silica cartridge (40 g) with a Combiflash Companion, eluting at 35 mL/min with a gradient running from 0 % EtOAc/hexanes to 50 % over 35 min. The desired fractions were concentrated under reduced pressure to give 450 mg (80 %) of the title compound. LC-MS m/z 220.9 (M+H)+, 1.11 (ret. time).

According to the analysis of related databases, 31804-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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 29578-83-4, COA of Formula: C8H9BrO

A mixture of NBS (5.31 g, 29.83 mmol, 1.20 equiv), AIBN (2.04 g, 12.42 mmol, 0.50 equiv), Cd4 (100 mL), and 1-bromo-3-methoxy-5-methylbenzene (5.00 g, 24.87 mmol, 1.00 equiv) was stirred for 12 h at 80C under nitrogen. The reaction was then quenched by water, extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:100) to afford the title compound (6 g, 86%) as a light yellow solid.

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-Bromo-3-methoxy-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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 20781-20-8, Safety of (2,4-Dimethoxyphenyl)methanamine

a. Potassium carbonate (2.97 g, 21.5 mmol) was added to a mixture of 2- chloropyrimidine (2.1 g, 17.9 mmol), 2,4-dimethoxybenzylamine (3.0 g, 17.9 mmol) and acetonitrile (20 mL). The reaction mixture was heated at reflux for 16 h, allowed to cool to ambient temperature and partitioned between ethyl acetate (150 mL) and water (10 mL). The organic phase was washed with water (2 10 mL) and brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in diethyl ether (20 mL), washed with hexanes (20 mL) and purified by column chromatography, eluting with a 0-100% gradient of ethyl acetate in hexanes to afford A/-(2,4-dimethoxybenzyl)pyrimidin-2-amine as a pale yellow solid in 84% yield (3.70 g): MS (ES+) m/z 245.9 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,4-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); A1;,
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