Author: Jessica.F

Application of 113170-72-2, A common heterocyclic compound, 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, molecular formula is C7H6BrF3N2, 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.

Intermediate 8 : 7-brom -2-(6-fluoropyridin-3 -yl)-5 -(trifluoromethyl)- 1 H-benzimidazole To a mixture of 6-fluoronicotinaldehyde (2.5 g, 19.98 mmol), 3-bromo-5-(trifluoromethyl)benzene-l,2-diamine (4.84 g, 19.98 mmol) in DMF (40 ml) and water (4 ml) added potassium peroxymonosulfate (7.99 g, 12.99 mmol) in portions over 1 hour. The reaction mixture was stirred overnight under N2 then pour into water (50 ml), extract with 3×80 ml ethyl acetate. The organic layers were combined, washed with 2×25 ml of saturated brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Part of the product was crystallized from dichloromethane. The mother liquor was purified by reverse phase HPLC to afford 7- bromo-2-(6-fluoropyridin-3-yl)-5 -(trifluoromethyl)- 1 H-benzimidazole as brown solid. LC-MS (ES, m/z) Ci3H6BrF4N3 : 361; Found: 362 [M+H]+.

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; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (2012); A1;,
Bromide – Wikipedia,
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Reference of 393-37-3, 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 393-37-3 as follows.

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 4-Bromo-1-fluoro-2-(trifluoromethyl)benzene was borylated using the general procedure described above. The borylation reaction afforded product as colorless oil (0.229 g, 62%): 1H NMR (500 MHz, CDCl3) delta 8.02 (dd, J=2.5, 3.5 Hz, 1H), 7.78 (dd, J=2.5, 6.5 Hz, 1H), 1.36 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 162.9 (dd, J=1.9, 259.7 Hz), 143.1 (d, J=8.5 Hz), 132.8 (qd, J=1.9, 4.7 Hz), 121.7 (q, J=270.3 Hz), 120.0 (qd, J=33.1, 16.1, Hz), 116.3 (d, J=3.5 Hz), 84.7, 24.8; 19F NMR (470 MHz, CDCl3) delta 61.9, 106.4; 11B NMR (160 MHz, CDCl3) delta 29.3 (br s).

According to the analysis of related databases, 393-37-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
Bromide – Wikipedia,
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Application of 556-96-7, These common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, 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: Under a dry nitrogen atmosphere, a mixture of aryl bromide(1.0 mmol), K4Fe(CN)6 (0.22 mmol), base (1.0 mmol) and Pd(0)-EGCG-CF (2.0 mol%) in DMF (5 mL) was stirred at 130 C for 8 h (Table 2). After completion (as monitoredby TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography. All of the desired product(s) were characterized by comparison of their physical data with those of known compounds [4,5c,7]. The formation of aryl nitriles was confirmed by IR spectra, which showed one characteristic peak for the CN stretching band between 2225-2360 cm-1.

The synthetic route of 556-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bahari, Siavash; Letters in Organic Chemistry; vol. 10; 7; (2013); p. 523 – 526;,
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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. 58971-11-2, name is 3-Bromophenethylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromophenethylamine

Weigh 0.382 g (2 mmol) of 3,5-dichlorosalicylaldehyde was dissolved in 30 mL of ethanol, 285 muL (2 mmol) of 3-bromophenethylamine was added dropwise and stirred under reflux for two hours. After cooling the system, 0.22 g (1 mmol) of zinc acetate dihydrate and 0.168 g (2 mmol) of sodium bicarbonate were added and the mixture was refluxed for two hours. The solution is cooled to produce a large amount of yellow precipitate.Filtered, rinsed three times with ethanol, and the precipitate was collected to give the crude product. The crude product was added to a tetrahydrofuran solution, dissolved by heating, and slowly precipitated a yellow solid at room temperature.Filtration gave product complex 2 (0.453 g, yield 55.9%).

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; Jilin University; Men, guangwen; (14 pag.)CN104262195; (2016); B;,
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Reference of 348-57-2,Some common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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 stirred solution of l-bromo-2,4-difluorobenzene (0.9 mL, 8.01 mmol) in diethyl ether (50 mL) was added dropwise n-BuLi (5 mL , 8.01 mmol; 1.6 M solution) at -78 C under an inert atmosphere. After being stirred for 40 min at -78 ¡ãC, a solution of T (2.1 g, 8.01 mmol) in diethyl ether (50 mL) was added dropwise to the reaction mixture at -78 ¡ãC. Stirring was continued for another 20 min. After completion of the reaction (by TLC), the reaction mixture was quenched with saturated NH4C1 solution and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography (eluent: 15-55percent EtOAc/hexanes) to afford ketone U (2.15 g, 6.24 mmol, 77.9percent). 1H NMR (200 MHz, CDCI3): delta 8.61 (d, J= 1.6 Hz, 1H), 7.96 (dd, J= 8.0, 1.6 Hz, 1H), 7.67-7.62 (m, 1H), 7.48 (d, J= 8.0 Hz, 1H), 6.98-6.67 (m, 2H), 1.98 (d, J F,H = 24.0 Hz, 3H). MS (ESI): m/z 343.9 [M+l] +.

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

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William J.; SCHOTZINGER, Robert J.; RAFFERTY, Stephen W.; WO2013/109998; (2013); A1;,
Bromide – Wikipedia,
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These common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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. SDS of cas: 1647-23-0

Example 42 9-(3,3-Dimethylbutyl)-7-methoxy-l,2,3,9-tetrahydro-4H-carbazol-4-one; 7-methoxy-l,2,3,9-tetrahydro-4H-carbazol-4-one from Example 41 Step B in 1 mL anhydrous DMF were added 27.2 mg l-bromo-3,3-dimethylbutane and 53.8 mg cesium carbonate. The reaction mixture was heated at 45C for 1 hour and at 35C for 3 days. After cooling to room temperature, the reaction mixture was diluted with 1: 1 dioxane and water and purified on RP-EtaPLC using 60-100% MeCN gradient in water with 0.1% TFA. The title compound was obtained as a colorless solid following lyophilization. LC-MS: 3.66 min. (m/Z = 300.2, 322.1).

The synthetic route of 1-Bromo-3,3-dimethylbutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/44232; (2006); A1;,
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Synthetic Route of 16518-62-0, 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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred mixture of FeCl36H2O (270.3 mg, 1.0 mmol) and2.0 mL toluene was added aniline 1 (0.4 mmol) at room temperature.The reaction mixture was stirred at 85 C for 2 h in atmosphere.After it was cooled to room temperature, the reactionmixture was quenched by aqueous ammonia solution (mass fraction:25e28percent, 10 mL) and extracted with dichloromethane (10 mLper time) until no product was observed in the extract, monitoredby TLC. The organic layer was dried over anhydrous MgSO4, filtered,and concentrated under reduced pressure to give crude product,which was chromatographed on silica gel column using 1:100 to1:70 (v/v) EtOAc/petroleum ether solutions as eluent to affordisolated product 2.

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-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Jing; Li, Jiaqiang; Huang, Ruofeng; Zhang, Xiaohui; Shen, Hang; Xiong, Yan; Zhu, Xiangming; Tetrahedron; vol. 71; 33; (2015); p. 5341 – 5346;,
Bromide – Wikipedia,
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These common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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. Product Details of 103273-01-4

30.0 g (157.88 mmol) 2-bromo-4-tert-butylaniline, 34.6 g (157.88 mmol) 4-bromobenzoyl chloride And 300 mL THF was added and stirred at room temperature for 3 hours. After the reaction is completed, the solvent is distilled off under reduced pressure. Solidification with diisopropyl ether (IPE) gave 42.6 g (yield: 72.3%) of a white solid compound (intermediate (37)).

The synthetic route of 2-Bromo-4-(tert-butyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Raepto Co., Ltd.; Seok Mun-gi; Go Byeong-su; Im Cheol-su; Kim Hyeon-a; Kim Gyu-sik; Park Yong-pil; Han Gap-jong; Oh Yu-jin; (37 pag.)KR102059550; (2019); B1;,
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Reference of 7766-50-9,Some common heterocyclic compound, 7766-50-9, name is 11-Bromo-1-undecene, molecular formula is C11H21Br, 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: p-Benzenediol (Hydroquinone, defined as BP1 here) (2.2 g,20 mmol) and sodium hydroxide (2.4 g, 60 mmol) were dissolved in 120 mL DMF in a 250-mL round bottomed Schlenk flask, then themixture was stirred for 30 min, and a solution of 11-bromo-1-undecene (12 g, 51.5 mmol) in DMF (120 mL) was added dropwise over 10 min. The resulting reaction mixture was heated at 70 C and left stirring for more than 8 h. Subsequently, the reaction was cooled to RT and quenched with addition of diethyl ether (100 mL) and water (100 mL). The aqueous phase was extracted with diethyl ether (300 mL 2), and the combined organic fractions were washed with brine and dried over MgSO4 and concentrated. The residue was recrystallized from EtOH twice to obtain 6.1 g BP1-M1. Yield: 74%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 11-Bromo-1-undecene, its application will become more common.

Reference:
Article; Song, Shaofei; Miao, Weijun; Wang, Zongbao; Gong, Dirong; Chen, Zhong-Ren; Polymer; vol. 64; (2015); p. 76 – 83;,
Bromide – Wikipedia,
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Related Products of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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 stirred solution of 2-bromo-3-fluoroaniline (CAS 111721-75-6, 9.50 g, 50.0 mmol, 1.00eq.) in an aqueous hydrochloric acid solution (12.5 mL conc. HCI in 80.0 mL of water, 150mmol, 3.00 eq.) was added dropwise a 2.5 M solution of sodium nitrite (20.0 mL, 50.0 mmol,1 .00 eq.) in water at a temperature of 0C. After complete addition, a 4.5 M solution of sodiumacetate in water (62.4 mL, 281 mmol, 5.62 eq.) was added via dropping funnel, followed bydropwise addition of ethyl-2-oxocyclopentanecarboxylate (CAS 611-10-9, 7.40 mL, 50.0 mmol,1.00 eq.). The resulting yellow suspension was maintained at 0 C for 15 minutes and thenwarmed to room temperature and stirred for 2 hours. The reaction mixture was extracted thricewith dichloromethane (100 mL each) and the combined organic extracts were dried overmagnesium sulfate, filtered and concentrated under reduced pressure to give the crudehydrazone as a red oil (18.1 g). The residue was dissolved in ethanol (50.0 mL, 1.00 M), afterwhich sulfuric acid (6.63 mL, 125 mmol, 2.50 eq.) was added dropwise. The dark orangesolution was heated at 95 C for 6 days and then cooled to room temperature. The dark brownsolution was poured onto ice/water (200 mL) and extracted thrice with dichloromethane (200mL each). The combined organic extracts were washed with saturated aqueous bicarbonatesolution (200 mL), dried over magnesium sulfate, filtered and concentrated under reducedpressure to give a brown solid. The residue was purified by flash column chromatography (0-30% ethyl acetate/hexane gradient) and then recrystallized from hot ethyl acetate/hexane (9:1)to give the title compound as a light yellow solid (8.35 g, 42%). Rf = 0.22 (15% ethyl acetate/hexane, UV).

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; WITTROCK, Sven; MCKINNEY, David; SERRANO-WU, Michael, H.; LEMKE, Chris; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; (652 pag.)WO2019/96922; (2019); A1;,
Bromide – Wikipedia,
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