Tag: M.W=200-300

38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, 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. Product Details of 38380-85-7

7?-BuLi (2. 5 M in hexane, 9.76 mL, 24.4 mmol) was added over 17 min to a solution of l-bromo-4-cyclopropoxybenzene (5.0 g, 23.4 mmol) in THF (80 mL) at -78 0C. After 40 min, B(OEt)3 (5.9 mL, 34.3 mmol) was added and the mixture was allowed to reach rt and was stirred at rt for 18 h. The mixture was cooled to 0 0C and HCl (aq, 1 M, 70 mL) was added. After 30 min the mixture was extracted with f-BuOMe (3×50 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was washed with petroleum ether to yield the sub-title compound (1.5 g, 34 %).

The synthetic route of 38380-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77367; (2006); A1;,
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Reference of 18800-30-1, 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. 18800-30-1 name is 1-Bromo-4-(2-bromoethoxy)benzene, 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.

EXAMPLE 6 1-(5-Amino-4H-1,2,4-triazol-3-yl)-4-[2-(4-bromophenoxy)ethyl]piperazine A mixture of 56.0 g (0.2 moles) of 2-bromoethyl p-bromophenyl ether and 45.6 g (0.4 moles) of 1-formylpiperazine in 500 ml of 2-propanol was heated at reflux for 18 hours. The mixture was cooled and filtered. The filter was washed with 2-propanol and the filtrate was evaporated to an oil in vacuo. Water was added and the oil was extracted three times with about 200 ml of chloroform. The extracts were combined, dried over magnesium sulfate and filtered. The filtrate was evaporated to an oil to which 250 ml of 5N sodium hydroxide was added. The mixture was refluxed for 18 hours, cooled and extracted three times with about 200 ml of chloroform. The extracts were combined, dried over magnesium sulfate and evaporated to an oil. The oil was distilled, bp 125-128 C./0.05 mm of mercury, and gave 40 g of 1-[2-(4-bromophenoxy)ethyl]-piperazine as a yellowing oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(2-bromoethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US4582833; (1986); A;,
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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 458-50-4 as follows. category: ethers-buliding-blocks

1-bromo-2-fluoro-4-methoxybenzene (5.0 g, 24 mmol) was dissolved in concentrated sulfuric acid (20 mL), and then potassium nitrate (2.40 g, 23 mmol) was added portionwise to the reaction mixture. The mixture was stirred for two hours in an ice bath. After the reaction was completed, the reaction solution was poured into ice water. The aqueous phase was extracted with ethyl acetate (15 mL*3). The organic layer was washed with saturated sodium hydrogen carbonate (15 mL*2), brine (10 mL*2) The crude product was separated by column chromatography ( petroleum ether: ethyl acetate = 10:1). 1-Bromo-2-fluoro-4-methoxy-5-nitrobenzene (2.40 g, white solid, yield: 40%).

According to the analysis of related databases, 458-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); 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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 32338-02-6

General procedure: Appel?s salt and an aniline were allowed to stir in CH2CI2 (DCM) for 1 h at room temperature under a nitrogen atmosphere. The solution was then cooled to below 5 00 and base (preferably DBU orDBN) was added, dropwise over 30 mm, to the stirring solution maintained at 5 00 all under a nitrogen atmosphere. After the addition, the resulting mixture was stirred for 30 mm while allowing it to warm to room temperature, after which it was ref luxed at 40 C for 4 h. Upon cooling to room temperature (rt), ethyl acetate (EtOAc) was added. The reaction mixture was then washed with saturated NH4CIaq solution, and H20. The organic phase was dried over Na2SO4 and concentratedin vacuo. The crude material was purified by silica gel chromatography to provide the corresponding benzothiazoles.

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; UNIVERSITY OF CAPE TOWN; JARDINE, Moegamat Anwar; RYLANDS, Marwaan; (60 pag.)WO2019/21202; (2019); 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. 22722-98-1, name is Sodium bis(2-methoxyethoxy)aluminiumhydride, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

75.0 g (209 mmol) of tantalum pentachloride was suspended in 1,200 ml of ether, and 335 ml (228 mmol) of isopropyl magnesium bromide (0.68M THF solution) was added thereto. A solution of 41.9 g (419 mmol) of ethylcylopentadienyl lithium prepared from ethylcylopentadiene and butyl lithium in THF (240 ml) was added, followed by refluxing for 1 hour. The solvent was distilled away, and the residue was dried at 80C in vacuo for 8 hours to obtain a dark brown solid containing bis(ethylcyclopentadienyl)dichlorotantalum (Ta(EtCp)2Cl2). 1,060 ml of toluene was added to this dark brown solid, and the resulting mixture was ice-cooled. 187 ml (623 mmol) of a toluene solution (65 wt%) of sodium bis(2-methoxyethoxy) aluminum hydride was added dropwise to the mixture, and temperature was returned to room temperature, followed by stirring for 17 hours. 107 ml of water was added to the mixture, followed by stirring until foaming does not occur. Insoluble contents were filtered out, and the solvent was distilled away from the filtrate. 590 ml of hexane was added to the residue, the insoluble contents were filtered out. When the filtrate was cooled to -70C, a white solid was formed. The supernatant was removed, and the solid was washed with 24 ml of cold pentane two times to obtain a solid. The solid obtained was distilled in vacuo at 2.5 Pa/100C to obtain 7.79 g (yield: 10.1%) of a colorless liquid. When this liquid was cooled to room temperature, white crystals were formed. 1H-NMR (Benzene-d6, delta ppm) 4.79 (m, 4H, C5H4Et) 4.72 (t, J=2.5 Hz, 4H, C5H4Et) 2.38 (q, J=7.5 Hz, 4H, CH3CH2Cp) 1.06 (t, J=7.5 Hz, 6H, CH3CH2Cp) -0.88 (t, J=10.5 Hz, 1H, Ta-H) -2.42 (d, J=10.5 Hz, 2H, Ta-H) 13C-NMR (Benzene-d6, delta ppm) 114.91 (C5H4Et) 85.64 (C5H4Et) 84.44 (C5H4Et) 23.78 (CH3CH2Cp) 15.98 (CH3CH2Cp)

The synthetic route of 22722-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tosoh Corporation; SAGAMI CHEMICAL RESEARCH CENTER; EP1852438; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 38197-43-2, name is 2-Bromo-1-methoxy-3-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 38197-43-2, Computed Properties of C8H9BrO

To a solution of 2-bromo-3-methylphenol (10.0 g, 53.5 mmol) in DMF (60 ml) was added sodium hydride (2.78 g, 69.5 mmol) in small portions at 0 C, which was followed by addition of Mel (6.69 mL, 107 mmol). TLC showed formation of a slightly less polar spot right away. The reaction was diluted with EtOAc (400 mL), washed with water 3 times, dried over Na2S04, and concentrated. The crude product was used in the next step without further purification. To the flask charged with the above material and a stir bar was added CuCN (9.9 g, 109 mmol) and DMF (100 mL). The mixture was purged three times with nitrogen, and heated to 150 C for 24 hours. TLC showed formation of a more polar spot. . The reaction was cooled to RT, diluted with DCM (400 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4Oac and brine, dried over sodium sulfate, concentrated to afford a brownish solid (4.8g, 60% yield). The resulting nitrile was used in the following step without further purification. To a flask charged with the nitrile and a stir bar was added NBS (6.4 g, 36 mmol) and TFA (60 mL). The reaction was allowed to stir at RT for 16 hours. TLC showed clean formation of a slightly more polar spot. The solvent was removed under vacuum, and the residue was purified by silica gel flash chromatography. After removal of solvent, 3-bromo-6-methoxy-2-methylbenzonitrile was collected.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
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Reference of 74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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.

step 2-To a solution of R-27b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford R-28.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); 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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9BrO

Alternate synthesis: l-(2-phenoxyethyl)-lH-pyrazole-4-carbaldehydeSodium hydride (60%>, 6.3 g, 1.0 eq) was added to a solution of lH-pyrazole-4- carbaldehyde (15 g, 156 mmol) in DMF (150 ml) at 0C. The mixture was allowed to warm and was stirred at room temperature. (2-Bromoethoxy)benzene (30.2 g, 1 eq) was then added and the resulting mixture was stirred overnight at room temperature. It was quenched by addition of aqueous ammonium chloride, diluted with water and extracted with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated. The residue was purified by column chromatography using a hexane/EtOAc gradient (10: 1 to 0: 100). Pure fractions were combined and evaporated under reduced pressure to yield l-(2-phenoxyethyl)-lH-pyrazole-4-carbaldehyde (24 g, 71%).

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; REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir; WO2012/118782; (2012); 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. 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H15BrO2

As shown in FIG. 2, 3.3 mmol of 3-bromobenzaldehyde diethanol and 3.8 mmol of nitrile ethyl acetate were mixed and diluted with ethyl acetate to 10 mL, and then the resulting solution was reacted by continuous flow at a flow rate of 1 mL / min. The device was pumped into the first HPLC column (containing 1 g PS-perazine) and the second HPLC column (containing 1 g PS-N-SO3) in sequence, and the first and second HPLC columns were immersed in an oil bath at 50 C. and reacted for 3 hours. After the reaction was completed, the HPLC column was rinsed with ethyl acetate, the product was collected, ethyl acetate was evaporated, and recrystallized from ethanol to obtain a solid product with a yield of 91%.

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; Huaqiao University; Xiong Xingquan; Liao Xu; (11 pag.)CN110818592; (2020); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 74137-36-3, 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. 74137-36-3 name is 1,3-Dibromo-5-methoxybenzene, 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.

A solution of 1,3-dibromo-5-methoxybenzene (24.5 g, 92.13 mmol, 1 equiv) in Et2O (400 mL) under nitrogen, cooled to -78 oC and stirred for 20 min was added n-BuLi (2.5mol/L in THF, 44 mL, 1.20 equiv) dropwised at -78 oC. The reaction mixture was continued to stir for 1h at -78 oC followed by addition of DMF (8.1 g, 110.55 mmol, 1.2 equiv) dropwise. After stirring for 45 min at -78oC, the reaction was quenched with water (200 ml) carefully and extracted with EtOAc (500 mL) twice. The combined organic layers were concentrated under reduced pressure to give a mixture, which was further triturated with hexane (200mL) to afford 3-bromo-5-methoxybenzaldehyde (45-2) (14.5 g, 73.2%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; WANG, Wenyue; ASHCRAFT, Luke W.; (362 pag.)WO2019/144041; (2019); A1;,
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