Tag: M.W=200-300

Reference of 60789-54-0,Some common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, molecular formula is C11H15BrO, 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.

Reference Example 32 3-(4-Benzyloxybutoxy)-4-(morpholin-4-yl)benzaldehyde 3-Hydroxy-4-(morpholin-4-yl)benzaldehyde (0.28g) and potassium carbonate (0.38g) were suspended in N,N-dimethylformamide (2 mL). To the reaction mixture was added benzyl 4-bromobutylether (0.36g), and the mixture was stirred at 50C for 16 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesiumsulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5) to give the title compound (0.50g). 1H―NMR (CDCl3) delta ppm:

The synthetic route of 60789-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1698635; (2006); 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 261762-35-0 as follows. SDS of cas: 261762-35-0

Reference Example 97; 3,4-Difluoro-5-methoxybenzaldehyde; 1.58 M n-BuLi/hexane solution (1.4 ml) was added to a diethyl ether solution of 5-bromo-1,2-difluoro-3-methoxybenzene (497 mg) in an argon atmosphere at -70C, followed by stirring at that temperature for 1 hour. DMF (0.259 ml) was added, followed by stirring for 30 minutes. After completion of the reaction, water was added, followed by extraction with diethyl ether, washing with saturated brine, and drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the compound (317 mg) of Reference Example 97.

According to the analysis of related databases, 261762-35-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP1795524; (2007); A1;,
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Synthetic Route of 19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 suspension of 4-bromo-3-methoxyaniline (25 g, 124 mmol) in concentrated HCl (1.7 L) cooled to O0C was added sodium nitrite (11.1 g, 161 mmol) in water (250 mL) slowly over 30 minutes, keeping the temperature below 80C. After stirring for 2 hours, KJ (61.6 g, 371 mmol) in water (250 mL) was added to the resulting orange solution slowly over 30 minutes, keeping the temperature below 8C. The mixture was then warmed to RT and stirred a further 1.5 hours. The mixture was then filtered through a sintered glass wool funnel. The resulting solid was dissolved in EtOAc (1.2 L) and washed with water, 0.5 N NaOH, aqueous sodium bisulfite, and brine. The organic layer was then dried over Na2SO4 and filtered through a pad of silica, and then solvent was removed in vacuo. The crude material was purified on silica (100% hexanes) to yield the title product.

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
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Application 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.

Example 17 Synthesis of ethyl (E)-3-(3-bromo-5-methoxyphenyl)acrylate (17-1) Step One: To a solution of 3,5-dibromoanisole (1.01 g, 3.79 mmol) in acetonitrile (20 mL) at room temperature under nitrogen, palladium(II) acetate (42 mg, 0.19 mmol), tri(o-tolyl)phosphine (116 mg, 0.38 mmol), ethyl acrylate (0.36 mL, 3.38 mmol) and triethylamine (2.10 ml, 15.1 mmol) were added sequentially. The mixture was heated to reflux 4 hours, cooled to room temperature, diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with 5percent ethyl acetate in hexanes. Fractions containing product were combined, concentrated and the residue was rechromatographed, eluting with 3percent increasing to 5percent ethyl acetate in hexanes to give ethyl (E)-3-(3-bromo-5-methoxyphenyl)acrylate (17-1, 354 mg) as a yellow oil.

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

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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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. 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, A new synthetic method of this compound is introduced below., Product Details of 157869-15-3

In a 10 mL reactor, add 2-((4-methoxyphenyl) ethynyl) aniline (111.6 mg, 0.5 mmol), phenylacetone (80.5 mg, 0.6 mmol), Cu (OAc) 2 (9.1 mg, 0.05 mmol), 2,2′-bipyridine (15.6 mg, 0.1 mmol), 4-OH-TEMPO (86.1 mg, 0.5 mmol) and 3 mL 1,2-dichlorobenzene. After heating at 120 C for 24 hours, the solvent was concentrated under reduced pressure to recover the solvent, which was separated (n-hexane / ethyl acetate = 50/1, v / v) to obtain 3- (2- (4-methoxyphenyl) as a white solid -1H-indol-1-yl) -1-phenylpropane-1-one (Id) (142.1 mg, 80%)

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; Zhejiang University of Technology; Ling Fei; Song Dingguo; Xiao Lian; Zhong Weihui; (9 pag.)CN111004164; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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 59557-91-4, Recommanded Product: 59557-91-4

To the solution of 4-bromo-2-methoxyaniline (2.00 g, 9.90 mmol) and 2- chloroacetaldehyde (1.87 g, 11.9 mmol) in methanol (20 mL), was added sodium cyanoborohydride (1.56 g, 24.7 mmol) and acetic acid (0.567 mL, 9.90 mmol). The mixture was stirred at rt overnight, then was concentrated. The product was purified byflash chromatography (0-50% EtOAc/hexanes gradient) to obtained 2.20 g (59% yield) ofIntermediate 3 as a yellow oil. MS(ESI)m/z: 264.3 (M+H) ?HNMR (300 MHz, CDC13)oe ppm 6.99 (dd, J=8.40, 2.12 Hz, 1 H) 6.89 (d, J=2.12 Hz, 1 H) 6.47 (d, J=8.45 Hz, 1 H)4.60 (s, 1 H) 3.87 (s, 3 H) 3.69 – 3.75 (m, 2 H) 3.51 (q, J=6.06 Hz, 2 H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; YADAV, Navnath Dnyanoba; BODAS, Mandar Shrikrishna; BHIDE, Rajeev S.; PATIL, Sharanabasappa; CHINNAKOTTI, Kumaresan; RAO, Prasanna Savanor Maddu; SHETTY, Jeevanprakash; (501 pag.)WO2016/112236; (2016); A1;,
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Reference of 38380-85-7, 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. 38380-85-7 name is 1-Bromo-4-cyclopropoxybenzene, 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.

Step 1: 1-bromo-4-(cyclopropyloxy)benzene (9.5 g, 45 mmol), DMA (66 mL), and MeOH (33 mL) were added to a bomb reactor and degassed by bubbling through argon for 5 minutes. The degassed mixture was charged with DPPF (1.85 g, 3.34 mmol) and Pd(OAc)2 (0.50 g, 2.2 mmol) and degassed under CO. The reaction was heated in the bomb at 15 psi CO at 80C for 18 h. The crude reaction mixture was filtered through celite and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel (5 – 25% EtOAc/hexane) to afford methyl 4-cyclopropoxybenzoate.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
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Reference of 116557-46-1, These common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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.

[00163] Intermediate 9B. (3-Bromo-2-methoxyphenyl)hydrazine: A suspension of Intermediate 9A (4.0 g, 20 mmol) in 6 M HC1 was cooled to -10 C and a solution of sodium nitrite (1.41 g, 20.8 mmol) in water (5 mL) was added slowly to keep the temperature below 0 C. After the addition, the reaction was stirred for additional 20 min at -10 C. A solution of tin (II) chloride (11.26 g, 59.39 mmol) in cone. HC1 (20 mL) was added slowly, resulting in precipitation. After 30 min, the precipitate was filtered, washed with cone. HC1 and then water, suspended in 10% NaOH solution, and extracted with EtOAc. The combined organics were dried over MgS04, filtered, and evaporated to give Intermediate 9B (1.8 g, 42%), which was used directly in the next step. LCMS (ESI) m/z 200, 202 (M-NH3+H, M-NH3+2+H)+, RT = 1.09 min (Method A).

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

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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Related Products of 452-08-4, The chemical industry reduces the impact on the environment during synthesis 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 107 9-Fluoro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 207, structure 41 of Scheme XI, where R1 =H, R2 =F) 5-Fluoro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =F) In a 200-mL flask, a solution of 2-bromo-4-fluoroanisole (Aldrich: 4.00 mL, 30.8 mmol) in THF (50 mL) was cooled to -78 C. (CO2 /IPA). To this solution n-BuLi (Aldrich: 2.5M in hexanes; 12.4 mL, 31 mmol, 1.0 equivuiv) was added dropwise over a 30 min period. The reaction mixture was stirred at -78 C. for 60 min and treated with trimethylborate (Aldrich: 10.5 mL, 92.4 mmol, 3.0 equivuiv). The reaction mixture was allowed to slowly warm to rt, stirred overnight (12 h), and cooled to 0 C. (ice/H2 O). The solution was treated with 5% HCl until the pH reached 6. The reaction mixture was poured into sat’d NH4 Cl (80 mL) and extracted with CH2 Cl2 (3*100 mL). The extracts were washed with sat’d NH4 Cl (1*80 mL), combined, dried (MgSO4), filtered through a pad of Celite, and concentrated to afford 4.90 g (94%) of a white semi-solid. Data for 5-fluoro-2-methoxyphenylboronic acid: 1 H NMR (400 MHz, acetone-d6): 7.47 (dd, J=8.8, 3.3, 1H); 7.17 (m, 1H); 7.05 (dd, J=9.0, 3.9, 1H); 3.93 (s, 3H).

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-fluoro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

To a solution of methyl isobutyrate 23 (5g, 49 mmol) in THF was added slowly a solution of LDA (52 mmol, generated from n-BuLi and diisopropyl amine) in THF at -78 0C, the reaction was stirred for 20 minutes. The resulting solution was treated with a solution of Benzyl 3-bromopropyl ether 22 in HMPA and stirred at -78 0C for 12 h, aq. HCI (1 N) was added and the resulting mixture extracted with ether, Organic layer washed with water, saturated NaHCO3, dried and concentrated, it was purified by to give the desired ester 24 (11.6 g, 80percent). 1HNMR (CDCI3) delta 7.36-7.26 (m, 5H), 4.49 (s, 2H), 3.65 (s, 3H), 3.45 (t, J = 6.5 Hz, 2H), 1.62-1.52 (m, 4H), 1.18 (s, 6H); 13C NMR (CDCI3) delta 178.3, 138.5, 128.3, 127.6, 127.5, 72.8, 70.5, 51.7, 42.0, 37.1 , 25.3, 25.1.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/158381; (2009); A1;,
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