Tag: M.W=200-300

Some common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, molecular formula is C9H11BrO, 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. Recommanded Product: 36449-75-9

b) At rt, a solution of 1-(2-bromo-ethyl)-2-methoxy-benzene (1.0 g, 4.15 mmol) inabs. THF (5 mL) is added to Mg turnings (0.13 g, 5.35 mmol) suspended in abs.THF (5 ml) over a period of 20 min. The thus obtained Grignard reagent is then added at to an ice-cold solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid methoxy-methyl-amide (400 mg, 1.5 mmol) in THF (5 ml). The reaction mixture is stirred at rt for 1 h, quenched by adding sat. aq. NhUCI (10 ml_), diluted with water (100 ml) and extracted twice with DCM (100 ml_). The combined organic extracts are dried over NaaSO/j, filtered and evaporated . The resulting residue is purified by prep. HPLC to afford 3-(2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2~trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]penta-len-4-yl)-propan-1-one (390 mg) as a colourless oil. LC-MS: tR = 1.15 min, [M+1f = 341.21; 1H NMR (CDCI3): 8 7.22-7.14 (m, 2H), 6.90-6.81 (m, 2H), 3.82 (s, 3H), 3.20-2.90 (m, 5H), 2.79 (d, J = 18.8 Hz, 1H), 2.38 (s, 3H), 1.88 (d, J = 2.9 Hz, 2H), 1.12 (s, 3H), 0.72 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36449-75-9, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; WO2006/10379; (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 886762-08-9 as follows. category: ethers-buliding-blocks

Into a 250-mL 3-necked round-bottom flask, was placed 5-bromo-2- (trifluoromethoxy) aniline (2 g, 7.81 mmol, 1 equiv), ethanol (20 mL), HCl (2 mL). This was followed by the addition of NaN02 (595 mg, 8.62 mmol, 1.10 equiv) dropwise with stirring at 0 C. To this was added water (110 mL), sulfuric acid (5.5 mL). The resulting solution was stirred for 1.5 h at 0 C in a water/ice bath. The resulting solution was allowed to react, with stirring, for an additional 12 h while the temperature was maintained at 100 C in an oil bath. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of sodium bicarbonate. The mixture was dried over anhydrous sodium sulfate. This resulted in 1 g (50%) of the title compound as an oil. Analytical Data: LC-MS: (ES, m/z): RT =1.715min, LCMS 53: m/z = 257 [M+l].

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6358-77-6, name is 5-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6358-77-6

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 1000 mg; 5.37 mmol; 1.0 eq.) and formic acid( 1.22 ml32.25 mmol; 6.0 eq.). RM is cooled down to 0 C and sodium formate ( 73.11 mg; 1.07 mmol; 0.2 eq.) is added in this temperature. RM is stirred at room temperature for 2 h. After this time RM is diluted with DCM and sodium formate is filtered off. Filtrate is washed, with water and saturated aqueous solution of NaHC03.0rganic solvent is dried over anhydrous Na2S04 overnight. After this organic solvent is evaporated to afford N-(5-bromo-2-methylphenyl)formamide ( 869.50 mg; yield 68.8 %; 91.0 % by UPLC) as a brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (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. 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Step C Preparation of 2-[3-(3-Methoxy-phenyl)-propyl]-malonic acid diethyl ester Diethylmalonate (7.65 mL, 0.050 mol) was added slowly to a vigorously stirred suspension of pre-washed NaH (60%) (2.4 g, 0.050 mol) in dry DMF (50 mL) at 0 C. under Ar. After 15 min, 3-(3-methoxyphenyl)propylbromide (11.5 g, 0.050 mol) was added slowly, the ice bath was removed, and the reaction mixture was stirred at 65 C. for 16 hr. The mixture was cooled, partitioned between EtOAc (250 mL) and H2O (200 mL), the organic layer washed with H2O (2*500 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound. FAB MS(M+1) 309.1

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; deSolms, S. Jane; Stokker, Gerald E.; Shaw, Anthony W.; US2002/99007; (2002); A1;,
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Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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. HPLC of Formula: C10H12BrFO

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 944317-92-4, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Synthetic Route of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Preparation GW-(2,6-diethylphenyl)-5-[(2E)-3-(dimethyta [(VI) R2 =Me, R3 = CONHR”, R” = 2,6-diethylphenyl]step 5To a solution of 5-acetyl-/V-(2,6-diethylphenyl)-1-methyl-1 H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), A/,A/-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80C for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2S04, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017g, 78% yield).1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1 H), 7.71 (d, J =12.33 Hz, 1 H), 7.36 (s, 1 H), 7.21 (t, J =7.60 Hz, 1 H), 7.12 (d, J =7.60 Hz, 2 H), 5.75 (d, J =12.33 Hz, 1 H), 4.18 (s, 3 H), 3.16 (s, 3 H), 2.92 (s, 3 H), 2.52 (q, J =7.57 Hz, 4 H), 1.09 (t, J =7.57 Hz, 6 H)HRMS (ESI) calcd for C20H27N4O2 [M +H]+ 355.2129, found 355.2133.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; CASUSCELLI, Francesco; BRASCA, Maria Gabriella; CALDARELLI, Marina; CERVI, Giovanni; DISINGRINI, Teresa; QUARTIERI, Francesca; WO2012/139930; (2012); A1;,
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Reference of 458-50-4, 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.

At 0 deg.C, 1-bromo-2-fluoro-4-methoxybenzene (5.00 g, 24.39 mmol) in sulfuric acid (20.0 mL) solution was added portionwise potassium nitrate (2.47 g, 24.39 mmol). The reaction mixture was stirred at 0 deg.C for 0.5 h. TLC (petroleum ether: ethyl acetate = 3: 1) indicated the reaction was complete. The reaction mixture was added to ice water (50.0mL) in the quenched (100mL × 2) and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and filtered, and concentrated to dryness under reduced pressure to give the title compound (5.55 g, 90% yield) as a white solid.

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; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 38603-09-7, name is 1,3-dibromo-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1,3-dibromo-2-methoxybenzene

To a THF solution of 2,6-dibromoanisole (10 g, 37.6 mmol) was added Mg (0.90 g, 37.6 mmol), and the mixture was heated and stirred at 40C. Under ice-cooling, n-heptanal (47.2 g, 41.3 mmol) was added dropwise. Aqueous hydrochloric acid solution was added to the reaction mixture, this was extracted with ethyl acetate, and the solvent was distilled off to obtain 8.95 g of a compound (1). NMR (CDCl3) delta ppm: 7.45 – 7.48 (m, 1H), 7.35 – 7.38 (m ,1H), 7.01 (t, 1H, 8.1 Hz), 4.96 – 5.00 (m, 1H), 3.88 (s, 3H), 1.70 – 1.80 (m, 2H), 1.25 – 1.63 (m ,8H), 0.85 – 0.90 (m, 3H)

The synthetic route of 38603-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi&Co., Ltd.; EP2184279; (2010); A1;,
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Electric Literature of 887267-47-2, The chemical industry reduces the impact on the environment during synthesis 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

The aryl halide (e.g., 1.00 mmol), triethylamine (e.g., 2.00 mmol) and P(o-tol)3 (e.g., 0.30 mmol) were dissolved in acetonitrile (e.g., 0.5 M) in a glass pressure tube and nitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes. Ethyl acrylate (e.g., 1.25 mmol) and palladium acetate (e.g., 0.10 mmol) were added to the reaction mixture and the tube was sealed and placed into an oil bath pre-heated to about 120 0C for about 18 h. The resulting solution was concentrated under vacuum and purified (e.g., silica gel column).The title compound was prepared from 2-bromo-5-(trifluoromethoxy)aniline according to protocol M. Retention time (min) = 2.693, method [1], MS(ESI) 276.1 (M+Eta).

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-5-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, 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 887267-47-2, Computed Properties of C7H5BrF3NO

To a solution of 2-bromo-5-(trifluoromethoxy)benzenamine (1.0 g, 3.9 mmol) in 20 mL of tetrahydrofuran were added /V,//-dimethylpyridin-4-amine (50 mg, 0.4 mmol), and di-tert-butyl dicarbonate (2.55 g,11.7 mmol). The resulting mixture was stirred at reflux for overnight. After cooled to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give 1.4 g (80%) of the product as a white solid. MS (ESIpos): m/z = 456 (M+H)+; LC-MS [Method 2] : R, = 1.07 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; NGUYEN, Duy; WORTMANN, Lars; FARIA ALVARES DE LEMOS, Adelaide, Clara; BOeMER, Ulf; SUeLZLE, Detlev; HOLTON, Simon; LECHNER, Christian; (147 pag.)WO2019/170543; (2019); A1;,
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