Category: 75148-49-1

Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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 75148-49-1, Quality Control of 3-Bromobenzaldehyde Diethyl Acetal

Step 1: Preparation of 3-(3-fluorooxetan-3-yl)benzaldehyde 3-Bromobenzaldehyde diethyl acetal (1 mL, 4.9 mmol) in dry THF (10 mL) at -78 C. was added 1.6M n-butyl lithium in hexanes (3.4 mL, 5.4 mmol) dropwise. The reaction mixture was stirred at -78 C. for fifteen minutes then added oxetan-3-one (0.353 g, 4.9 mmol) dropwise. The reaction mixture was stirred at -78 C. for thirty minutes. The reaction mixture was diluted with 50 mL saturated ammonium chloride solution and 50 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate, concentrated under reduced pressure to give the desired product, and purified by silica gel chromatography with a gradient to 50% ethyl acetate/hexanes. The crude mixture was dissolved in dry dichloromethane (10 mL), cooled to -78 C., and added diethylaminosulfur trifluoride (0.16 mL, 1.1 mmol) dropwise. The reaction mixture was stirred at -78 C. for thirty minutes. The reaction mixture was warmed to room temperature. The reaction mixture was diluted with 50 mL 1M sodium hydroxide and 50 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography with a gradient to 30% ethyl acetate/hexanes to give the desired product as a clear colorless oil (0.051 g, 0.28 mmol). 1H NMR (400 MHz, dichloromethane-d2) delta 10.10 (s, 1H), 8.13-8.10 (m, 1H), 7.96-7.92 (m, 1H), 7.92-7.88 (m, 1H), 7.72-7.66 (m, 1H), 5.20

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Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
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Reference of 75148-49-1,Some common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, molecular formula is C11H15BrO2, 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. 3-iodobenzaldehyde diethyl acetal. To a stirred -78 C. solution of 3-bromobenzaldehyde diethyl acetal, prepared as in step 1, (1.0 g, 3.8 mmol) in THF (10 mL) was added n-butyllithium (1.7 mL, 4.25 mmol, 2.5M in hexanes). The cold reaction mixture was stirred 0.5 hours followed by the addition of a THF (5 mL) solution of iodine (1.09 g, 4.25 mmol). The ice bath was removed and the reaction allowed to warm to ambient temperature. Saturated NH4 Cl was added and the mixture diluted with hexanes. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel eluding with 5% ethyl acetate-hexanes to afford 1.0 g of 3-iodobenzaldehyde diethyl acetal.

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

Reference:
Patent; Abbott Laboratories; US5616596; (1997); A;,
Ether – Wikipedia,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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. category: ethers-buliding-blocks

In an open ChemGlass vial with pressure -release top, a stirred mixture of 3- bromobenzaldehyde diethylacetal (Aldrich, St. Louis, MO) (65 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′- diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and trans-2- (trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred overnight. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtO Ac (20 mL), filtered through Celite and the filter cake washed with EtO Ac (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (3 prep TLC plates used) using EtOAc / hexane (1:4) as eluent to give the product (58.6 mg, 69% – yield adjusted for purity) as an oil [note: desired product contaminated with another compound after prep TLC – approximately 85% pure by 1H NMR and LC/MS].[00221] 1H NMR (CDC13, 300MHz): delta 7.34-7.24 (m, 3H), 7.08 (dt, / = 7.1, 1.7 Hz, 1H), 5.46 (s, 1H), 3.67-3.48 (m, 4H), 2.40-2.34 (m, 1H), 1.88-1.75 (m, 1H), 1.40-1.31 (m, 1H), 1.24 (t, 7 = 7.1 Hz, 6H), 1.20-1.14 (m, 1H). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = no mass-ion by LC/MS or HRMS.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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 75148-49-1, Quality Control of 3-Bromobenzaldehyde Diethyl Acetal

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

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, 3-Bromobenzaldehyde Diethyl Acetal, other downstream synthetic routes, hurry up and to see.

Related Products of 75148-49-1,Some common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, molecular formula is C11H15BrO2, 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.

7c) In analogy to Example 7a), from 1-bromo-3-diethoxymethyl-benzene (Example 6c)) and ethyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[[(trifluoromethyl)sulphonyl]oxy]-quinoline-3-carboxylate there is obtained ethyl 1-cyclopropyl-7-(3-diethoxymethyl-phenyl)-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylate as a colourless solid. Yield: 44%. Mass spectrum: peaks: inter alia at 453 (M+, 16%), 408 (21%), 381 (100%).

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

These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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. Formula: C11H15BrO2

Step 1: Preparation of 3-(3-aminooxetan-3-yl)benzaldehyde Hydrochloride 3-Bromobenzaldehyde diethyl acetal (11.65 g, 45 mmol) in dry THF (100 mL) at -78 C. was added n-butyl lithium (2.5 M in hexanes, 19 mL, 47 mmol) dropwise. The sample was stirred at -78 C. for ten minutes then added 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfonamide (7.5 g, 43 mmol) dropwise. The sample was stirred at -78 C. for one hour. The mixture was diluted with 200 mL saturated ammonium chloride solution and 200 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate (250 mL). The reaction mixture was cooled to 0 C. was added 1M hydrochloric acid in ethyl acetate dropwise (24 mL, 24 mmol). The reaction mixture was stirred at 0 C. for one hour then vacuum filtered to give the desired product as a slightly off white solid (1.97 g, 9.2 mmol). 1H NMR (400 MHz, DMSO-d6) delta 10.08 (s, 1H), 9.18 (s, 3H), 8.09 (s, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.79-7.73 (m, 1H), 5.03-4.91 (m, 4H).

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

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Ether – Wikipedia,
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Electric Literature of 75148-49-1, 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. 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

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

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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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

Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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 75148-49-1, 75148-49-1

To a solution of 3-bromobenzylaldehyde diethyl acetal (0.518 g, 2.0 mmol) and15 anhydrous toluene (4 ml) was added 1-methylpiperazine (0.240 g, 2.4 mmol) followedby Pd2(dba)3 (0.018 g, 0.02 mmol), racemic BINAP (0.037 g, 0.06 mmol) and Na01Bu(0.326 g, 3.4 mmol). The reaction mixture was placed into an oil bath preheated to 100C and stirred at this temperature for 18 h under argon, then allowed to cool to roomtemperature. Aqueous HCI (1M; 10 ml) was added, the mixture was vigorously stirred20 for 2.5 h, then the pH adjusted to 13 with 6M aqueous NaOH and extracted with ethylacetate (3 x 30 ml). The combined organics were dried (Na2S04), concentrated in vacuoand the residue was absorbed on silica gel and placed on a 10 g isolute column. Elutionwith ethyl acetate I dichloromethane (v/v; 4:1) and then a gradient of methanol (3 to 7%)in ethyl acetate afforded the title compound as a yellow oil (0.170 g, 42%). 1 H-NMR (50025 MHz, DMSO-d6) 2.22 (s, 3H, N-Me), 2.46 (t, J = 5.0 Hz, 4H, piperazine C-H), 3.21 (t, J =5.1 Hz, 4H, piperazine C-H), 7.28 (m, 2H, PhH), 7.41 (m, 2H, PhH), 9.94 (s, 1 H, CHO);[00122] LC- MS (ESI, m/z): Rt = 0.86 min- 205 (M+Ht.

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, 3-Bromobenzaldehyde Diethyl Acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); A1;,
Ether – Wikipedia,
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75148-49-1, These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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.

To a mixture of 3-bromobenzaldehyde diethylacetal (1.495 g, 5.77 mmol) and bis(triphenylphoshine)palladium(II) dichloride (206 mg, 0.29 mmol) in dimethoxyethane (30 mL) at room temperature under nitrogen, 2-thiopheneboronic acid (1.189 g, 9.29 mmol) and aquesou sodium bicarbonate (1M, 29 mL) were added. The mixture was heated to reflux overnight, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give a mixture of 2-(3-(diethoxymethyl)phenyl)thiophene and 14-1. This material was taken up in 1:1 methanol:water (30 mL) and concentrated sulfuric acid (1 mL) was added. The mixture was heated to reflux for 2 hours, cooled to room temperature and concentrated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and concentrated.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 75148-49-1.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
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