Month: February 2021

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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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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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. 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, A new synthetic method of this compound is introduced below., name: 1-Isopropoxy-2-vinylbenzene

A vacuum dried Schlenk flask was charged with imidazolium hydrochloride salt 4b (129 mg, 0.26 mmol, 1.15 eq.) and 10 mL dry toluene was introduced into the flask using a syringe. The white suspension thus formed was vigorously agitated and to it was introduced under an argon atmosphere solid KHMDS (95 %, 60 mg, 0.28 mmol, 1.23 eq.). The suspension turned homogeneous and was left to stir for 30 min. To this was then introduced, under an argon atmosphere, Grubbs first generation catalyst (190 mg, 0.23 mmol, 1.0 eq.) and the mixture was left stirring for another 2 hours at room temperature. The toluene was then evaporated in vacuuo to give a dark brown coloured semisolid. No purification of this mixture was attempted, however as significant degradation and loss of intermediate complex was observed. The crude brown semisolid was then redissolved in 10 mL of DCM and to this was introduced CuCl (91 mg, 0.92 mmol, 4 eq.) and 1-isopropoxy-2-vinylbenzene (75 mg, 0.46 mmol, 2 eq.) and the mixture stirred at 40C for 3 hours. The reaction was then cooled and DCM evaporated in vacuuo to give a dark green coloured semisolid. The semisolid was first washed with dry, distilled pentane (2¡Á50 mL) and dried under high vacuum. The resulting green powder was loaded onto a column of silica gel soaked in pentane. This was then eluted successively using pure pentane to remove unreacted vinylbenzene and then a 1/1 mixture of pentane/DCM and finally pure DCM to remove a green band which was collected and dried under high vacuum to yield a green coloured amorphous powder. C41H58N2OCl2Ru (766.88) calc. for C 64.21, H 7.62, N 3.65, found C 64.36, H 7.68, N 3.49.

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:
Article; Shahane, Saurabh; Toupet, Loic; Fischmeister, Cedric; Bruneau, Christian; European Journal of Inorganic Chemistry; 1; (2013); p. 54 – 60;,
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Synthetic Route of 82830-49-7,Some common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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 10 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 3-bromo-2,4,6-triisopropyl-4?-(trifluoromethyl)-1,1?-biphenyl (852 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h (A). In another 10 mL oven-dried Schlenk tube was charged with 2-fluoro-1,4-dimethoxybenzene (156 mg, 1 mmol) and anhydrous THF (3.5 mL). The tube was cooled to -78 C. and 1.6 M n-BuLi solution in hexane (0.64 mL, 1 mmol) was added dropwise over 10 min under vigorous stirring. The mixture was stirred at -78 C. for 40 min (B). A was transferred into to B by syringe over 15 min at -78 C. An additional 1 mL of THF was used to rinse the reaction and was also transferred to B. The combined reaction mixture was stirred at -78 C. for another 1 h and then slowly warmed to room temperature and vigorously stirred for overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (762 mg, 3 mmol) in 4 mL anhydrous THF was added drop-wise over 5 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (10 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (226 mg, 37%), labeled as 25MeOTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.66-7.61 (m, 3H), 7.46-7.39 (m, 2H), 7.23 (s, 1H), 6.90 (d, J=8.9 Hz, 1H), 6.82 (d, J=8.9 Hz, 1H), 3.91 (s, 3H), 3.71 (s, 3H), 2.65 (p, J=7.2 Hz, 1H), 2.37 (dp, J=25.3, 6.9 Hz, 2H), 1.23 (d, J=6.8 Hz, 3H), 1.11 (dd, J=10.3, 6.9 Hz, 6H), 1.04 (d, J=6.9 Hz, 3H), 0.80 (d, J=7.2 Hz, 3H), 0.71 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, Chloroform-d) delta 152.40 (d, J=40.7 Hz), 147.01, 146.10, 145.85, 141.68, 137.11 (d, J=48.9 Hz), 136.32, 132.12, 131.30, 128.68 (d, J=32.3 Hz), 124.02, 119.94, 110.00, 109.30, 56.81, 55.31, 32.51, 30.93, 29.72, 24.61 (d, J=4.2 Hz), 24.00, 23.69, 22.94 (d, J=12.1 Hz) ppm. 19F NMR (376 MHz, CDCl3) delta=-62.15 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-1,4-dimethoxybenzene, its application will become more common.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); 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. 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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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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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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Related Products of 6851-80-5, 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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Methoxyphenyl)-N-methylmethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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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 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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 the product from step 46 2 (1.00 g, 5.29 mmol) in 94 ACN (20 mL) was added 43 bis(2-methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 C. for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCl3) delta 7.47 (bs, 2H), 3.77 (t, J=5.7 Hz, 4H), 3.52 (t, J=5.4 Hz, 4H), 3.25 (s, 6H). 13C NMR (75 MHz, CDCl3) ? 154.7 (s), 152.0 (s), 120.9 (s), 119.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t). LCMS (50-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=4.91 min on 250 mm column, (M+H)+=286, (M+Na)+=308, (M+Na+ACN)+=349.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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