Category: 6358-77-6

Related Products of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-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.

Step 1. Synthesis of 1 -(5-bromo-2-methoxyphenyl)-5-methyl-1 H-pyrazole (C14). Boron trifluoride-tetrahydrofuran complex (777 g, 5.55 mol) was slowly added to a solution of 5-bromo-2-methoxyaniline (799.8 g, 3.96 mol) in 2-methyltetrahydrofuran (5.3 L), and the mixture was filtered through Celite. The filtrate was brought to a volume of 9 L with additional 2-methyltetrahydrofuran. In a separate container, tert-butyl nitrite (433 g, 4.20 mol) was dissolved in 2-methyltetrahydrofuran (8.0 L); the volume was then adjusted to 9 L by addition of 2-methyltetrahydrofuran. The two solutions were pumped by two Ismatec syringe pumps, both of which had been calibrated to deliver 15 mL/minute of 2-methyltetrahydrofuran, into a T-mixer connected to a 240 ml_ polytetrafluoroethylene (PTFE) coil for diazonium salt formation. At a combined flow rate of 30 mL/minute, the reaction mixture had a total residence time of 8 minutes in the coil to facilitate complete diazonium salt formation. The syringe pumps were started simultaneously, and the material was passed through the coil into a two-stage continuous flow stirred-tank reactor, where the 5-bromo-2-methoxybenzenediazonium tetrafluoroborate product (C12) was continuously extracted into water, using a water pump with a flow rate of 20 to 22.5 mL/minute. The aqueous layer was continuously separated in a stand pipe decanter, and then quenched into a jacketed 20 L reactor containing a mixture of tin(ll) chloride dihydrate (2.28 kg, 12.0 mol), 2- methyltetrahydrofuran (4 L) and water (4 L) at zero C. When the reduction had provided complete conversion to (5-bromo-2-methoxyphenyl)hydrazine (C13), as monitored by HPLC analysis, a solution of (3E)-4-(dimethylamino)but-3-en-2-one (454 g, 4.01 mol) in 2-methyltetrahydrofuran (3.0 L) was charged, and the jacket temperature was adjusted to 20 C. After 14 hours, analysis of the organic layer indicated that hydrazine C13 had been consumed. The layers were separated, and the organic layer was washed with aqueous sodium hydroxide solution (6 N, 2 x 5 L). Silica gel (1 .0 kg) was added to the organic phase, and the mixture was concentrated to dryness and dried at 35 C and 100 mbar vacuum on a rotary evaporator until a free-flowing powder was obtained. This powder was loaded onto a pad of silica gel (100 g), and elution was carried out with 2- methyltetrahydrofuran (6 L); the eluant was concentrated in vacuo to provide the product as a thick dark red oil. 1H NMR data indicated that this material was comprised of a roughly 9:1 ratio of the title product and the regioisomeric pyrazole. Yield: 573 g, 2.15 mol, 67% (corrected for 80% purity of starting 5-bromo-2-methoxyaniline). GCMS m/z 266, 268 (M+). 1H NMR (400 MHz, CDCI3) title product peaks only: delta 7.60 (d, J=1 .8 Hz, 1 H), 7.52 (dd, half of ABX pattern, J=8.7, 2.4 Hz, 1 H), 7.49 (d, half of AB pattern, J=2.4 Hz, 1 H), 6.92 (d, J=8.7 Hz, 1 H), 6.16-6.18 (m, 1 H), 3.79 (s, 3H), 2.16 (br s, 3H).

Statistics shows that 5-Bromo-2-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 6358-77-6.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; WO2012/172449; (2012); A1;,
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These common heterocyclic compound, 6358-77-6, name is 5-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. Computed Properties of C7H8BrNO

(w) By proceeding in a similar manner to Reference Example 4(a), method A, but using cyclopropyl cyanide and 5-bromo-2-methoxyaniline (Reference Example 50), there was prepared 1-bromo-3-(cyclopropyl-imino-methylamino)-4-methoxybenzene.

The synthetic route of 5-Bromo-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US6303600; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-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 6358-77-6, HPLC of Formula: C7H8BrNO

To a stirred 100 mL RBF was added 5-bromo-2-methoxyaniline (7 g, 34.6 mmol) and DIEA (12.05 mL, 69.3 mmol) in DCM (100 mL). At 0 C, furan-2-carbonyl chloride (3.41 mL, 34.6 mmol) was added dropwise. The reaction mixture was stirred at 0 C and allowed to warm to RT overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo. The sample was preloaded on silica and purified with flash chromatography on a CombiFlash silica gel column (80 g, Teledyne Isco, gradient 20% EtOAc in hexanes) to give Example 209.1. LCMS (ESI) m/z= 297 [M+Hf?.

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

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Reference of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: Preparation of (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

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; Ty, Nancy; Pontikis, Renee; Chabot, Guy G.; Devillers, Emmanuelle; Quentin, Lionel; Bourg, Stephane; Florent, Jean-Claude; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1357 – 1366;,
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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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-methoxyaniline

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 1.00 g, 4.95 mmol), 3-chloro-4-methylphenylboronic acid (Acros, 1.69 g, 9.90 mmol), 1,1 ‘-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.81 g, 0.99 mmol), and purged with nitrogen. 1,4-Dioxane (37.1 ml) and an aqueous sodium carbonate solution (1.9 M, 12.4 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-4′-methyl-[l,l’-bipheny 1]-3-amine (1.03 g, 4.16 mmol, 84.0 % yield) as a tan solid.

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

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Electric Literature of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: A mixture of sydnone (1 eq.), aryl halide (1.5 eq.), palladium acetate (5mol %), XPhos (10mol%) and potassium carbonate (2 eq.) in DMF (0.5 M) under an atmosphere of nitrogen was heated at 80 C (for 3-alkylsydnones) or 120 C (for 3-arylsydnones) for 14 h before the reaction was allowed to cool to r.t. and water was added. The resulting mixture was extracted with ethyl acetate:40-60 petroleum ether (9:1) and the combined organic layers dried over MgSO4 and concentrated in vacuo. Flash silica chromatography (eluting solvent 20%-100% ethyl acetate in 40-60 petroleum ether) afforded the target 3,4-diarylsydnones. The compounds could be further purified by recrystallisation from ethanol or dichloromethane/petrol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Article; Brown; Harrity; Tetrahedron; vol. 73; 22; (2017); p. 3160 – 3172;,
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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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Application of 6358-77-6, 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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Preparation of (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-methoxyaniline. I believe this compound will play a more active role in future production and life.

Synthetic Route of 6358-77-6, The chemical industry reduces the impact on the environment during synthesis 6358-77-6, name is 5-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

Step 1: water (5 mL), boric acid (55 mg, 0.89 mmol) and glycerol (2-3 drops) were added to a stirred solution of 5-bromo-2-methoxyaniline (600 mg, 2.97 mmol) and divinylsulfone (351 mg, 2.97 mmol). The resulting mixture was stirred at reflux for 18h. The reaction mixture was cooled to rt and extracted withEtOAc. The organic layer was washed three times with water, dried over Mg504, filtered and the solution was evaporated under reduced pressure. Thecrude product was purified by silica gel column chromatography using Hexanes/EtOAc (50:50) as eluent yielding 4-(5-bromo-2-methoxyphenyl)-1- thiomorpholine-1,1-dione Ex.49a (900 mg, 95%). 1H NMR (400 MHz, DMSOd6, d in ppm): 3.22 (t, 4H, J=5.2Hz), 3.41-3.46 (m, 4H), 3.80 (s, 3H), 6.92-6.96(m, 1H), 7.12 (d, 1H, J=2.4Hz), 7.18 (dd, 1H, J=8.6Hz, J=2.4Hz).

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

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (144 pag.)WO2018/138359; (2018); A1;,
Ether – Wikipedia,
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Reference of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: To asolution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (e, 1.0 g 3.52 mmol) in ethanol (20 mL) was addedsubstituted aromatic amine (3.52 mmol) and acetic acid (1 drop). Themixture was refluxed for 3 h. Thereafter, the mixture was cooled toroom temperature, the precipitate was formed and filtered, washedwith ethanol and dried under reduced pressure to afford product l1-l14

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Article; Chen, Shaowei; Han, Yufei; Hou, Yunlei; Wang, Ruxin; Yan, Pingzhen; Ye, Tianyu; Zhao, Yanfang; Bioorganic Chemistry; vol. 99; (2020);,
Ether – Wikipedia,
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