Tag: M.W=100-200

Some common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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. Quality Control of 2-Bromo-5-fluoroaniline

2-Bromo-5- fluorobenzenamine (15 g, 78.94 mmol) was weighed into a 100 mL flask and dissolved in 100 mL of 6N HCl. The reaction mixture was heated to reflux, followed by dropwise addition of (E)-but-2-enal (6.87 ml, 83 mmol) mixed with 1.0 mL deionized water over 25 minutes. Following complete addition, the reaction was heated at 100 °C for an additional 35 minutes. The reaction was cooled to ambient temperature, followed by addition of 50 mL of Et2O. The reaction was stirred for 5 minutes followed by removal of Et2O by separatory funnel. ZnCl2 (3.587 g, 26 mmol) was added to the aqueous layer in two portions and the reaction mixture was cooled to 0 0C over 30 minutes. The aqueous layer was then taken to pH 8.0 using concentrated NH4OH. The aqueous layer was then extracted with Et2O and then EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo, affording the desired product 8-bromo-5-fluoro-2-methylquinoline (18.1 g, 95 percent yield) as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-99-2, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2008/121687; (2008); A2;,
Bromide – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 1575-37-7, name is 4-Bromobenzene-1,2-diamine, 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 1575-37-7. 1575-37-7

A 250 mL four-necked flask equipped with a mechanical stirrer, thermometer, reflux condenser, nitrogen inlet and bubble counterEach o-diaminobenzene (0.031 mol) (Formula 1a) was added dropwise to glacial acetic acid (50 mL) under a nitrogen atmosphere.The resulting slurry was cooled to 4 [deg.] C in an ice-bath. Sodium nitrite in water (6 mL) (2.24 g,0.032 mol) in THF Was added dropwise over 40 minutes while maintaining the temperature of the reaction mixture below & lt; RTI ID = 0.0 & gt; 10 C. & lt; / RTI & gt; GeneratedThe slurry was allowed to warm to room temperature and analyzed using a KI / amylose test paper until analysis for free HNO2 was negative and starting material was not visible in thin layer chromatography (16 h)Under stirring. The resulting slurry was filtered; the solid residue washed with water (100 mL) and the resulting solid was further purified by recrystallization from ethanol (20 mL). The product was dried for 24 h at 50 C. and 5 mbar and obtained as off-white solid. Yield: 67%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-Bromobenzene-1,2-diamine.

Reference:
Patent; BASF SE; Reihard, Robert; Kalor, Martin; Router, Michael; Li, Yuchuo; Cliff, Andreas; (31 pag.)KR2016/30566; (2016); A;,
Bromide – Wikipedia,
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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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5433-01-2

To a solution of Compound 59A (3.96 g, 20 mmol) in dry THF (20 mL) at – 78 C was dropped a solution of n-BuLi in THF (2.5 M, 8 mL, 18 mmol). After stirred at – 78 C for 1 hour, to the mixture was dropped N-methoxy-N-methylacetamide (1.87 g, 18 mmol). The mixture was stirred at -78 C for 0.5 hour, quenched with water (10 mL), and extracted with ethyl acetate (20 mL x 3). The combined organic layers was washed with brine (40 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 8% v/v) to yield Compound 59B: LC-MS (ESI) m/z: 163 [M+H]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) 1.27 (d, J =7.2.4 Hz, 6H), 2.60 (s, 3H), 2.93-3.00 (m, 1H), 7.38 (t, J = 7.6 Hz, 1H), 7.44 (t, J = 7.2Hz, 1H), 7.76 (d, J = 7.2 Hz, 1H), 7.83 (s, 1H).

The synthetic route of 5433-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; (552 pag.)WO2017/214505; (2017); A1;,
Bromide – Wikipedia,
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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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 53078-85-6

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous chloride (0.02 mmol), 2-bromo-5-methylaniline (0.2 mmol),1,10-azaphenanthroline (0.04 mmol), sodium carbonate (0.4 mmol), adding carbon disulfide (0.2 mmol), DMSO (2.0 mL) with a syringe under oxygen, and placing the reaction tube in a 110 C oil bath with stirring 6 hour. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (7:1 v/v)) to give the desired product 61.0 mg. The yield was 76%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53078-85-6.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Bromide – Wikipedia,
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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. 626-88-0, name is 1-Bromo-4-methylpentane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-methylpentane

To a solution of the 1H-indazol-5-ol (100 mg, 0.745 mmol) obtained in Reference Example 4 in N,N-dimethylformamide (2 ml) were added 1-bromo-4-methylpentane (0.109 ml, 0.745 mmol), tetrabutylammonium iodide (28 mg, 0.1 mmol) and potassium carbonate (103 mg, 0.745 mmol), and the resulting mixture was heated to 60C. After 9 hours, the mixture was poured into water (20 ml) and extracted with ethyl acetate (20 ml x 2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-[(4-methylpentyl)oxy]-1H-indazole (60 mg, 37%). Melting point: 124-126C

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; Sumitomo Pharmaceuticals Company, Limited; EP1403255; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

K3PO4 (212 mg, 1 mmol),aryl halides (0.5mmol) and phenylboronicacid (0.75 mmol) were added successively into a dried Schlenk tubewith a magnetic bar under nitrogen. Then a N,N-dimethylacetamide (DMA 0.05 mL) solution of tetraphosphine TPPDA (0.0005 mmol) andPdCl2 (0.0005 mmol), which was reacted at 100 C for 1 h prior to use,was added into the mixture. Afterwards, o-xylene (3 ml) was addedwith syringe. After being stirred for the required time in the preset con-ditions, the reaction mixture was cooled to room temperature. The mix-ture solution was extracted with ethyl acetate (3 5 mL). Combinedorganic phase was washed with brine (3 5 mL) and dried over anhy-drous MgSO4. The dried solution was ltered and puried by silica gelchromatography (petroleum ether 60-90 C) to give a correspondingproduct. Reaction condition: aryl halides 0.5 mmol, phenylboronic acid 0.75 mmol, K3PO4 1.0mmol, o-xylene 3 mL, catalyst PdCl2/TPPDA = 1/1, 90 C, under nitrogen, GC yields.

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

Reference:
Article; Guo, Fei-Chen; Zhou, Rong; Jiang, Zhi-Jie; Wang, Wei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 66; (2015); p. 87 – 90;,
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Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, belongs to bromides-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 656-64-4, HPLC of Formula: C6H5BrFN

Compound III (63.0g, 387.5mmol) and ethanol (300 mL) was added 1L three-necked flask, dissolved under stirring, 3-bromo-4-fluoroaniline (81.0g, 426.3mmol), was added dropwise at room temperature NaHCO3(81.4g, 969.1mmol) was dissolved in 250mL of water was added, was warmed to 60 , reaction was 12 hours (complete reaction was monitored by TLC); and the reaction solution was transferred to a 1L round-bottom flask, ethanol was evaporated under reduced pressure, the residue was The organic layer was extracted three times with ethyl acetate (200mL × 3) were combined, washed twice with saturated NaCl solution, dried over anhydrous Na2SO4Drying; filtration, the filtrate was concentrated under reduced pressure to dryness, ethyl acetate / hexane to, filtration, and drying 45 deg.] C to give 76.0 g white solid, a yield of 62.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; Zhu Qihua; He Guangchao; Dong Zhongxia; Shan Jinxi; Wang Junjie; Xu Kexin; Xu Yungen; (11 pag.)CN108101899; (2018); A;,
Bromide – Wikipedia,
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Synthetic Route of 583-70-0, 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. 583-70-0, name is 2,4-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: to a suspension of magnesium powder (239 mg, 9.79 mmol) in dry THF(small amount) was added dropwise 1 -bromo-2,4-dimethylbenzene (1.64 g, 8.86mmol) diluted in dry THF (20 mL) and the reaction was heated at 40C. Aftercompletion of Grignard reagent, 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide (995 mg, 4.66 mmol) diluted in THF (10mL) was added to the solution. The reaction mixture was stirred at rt overnight.Water was added to quench the reaction. The two layers were partitionated andthe organic layer was dried over Mg504, filtered and the solution wasconcentrated under reduced pressure. The crude material was purified by silicagel column chromatography using a gradient of hexanes/EtOAc ([5:1] to [4:1]) to afford N-[(2,4-di methyl phenyl)(5-methylfuran-2-yl)methyl]-2-methylpropane-2- sulfinamide (1 .27 g, 85%) as yellowish oil

The synthetic route of 2,4-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (82 pag.)WO2018/138354; (2018); A1;,
Bromide – Wikipedia,
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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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., Recommanded Product: (Bromomethyl)cyclopentane

To a solution of 3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1.71 (0680) mmol) in anhydrous DMF (5 mL) was added K2C03 (355 mg, 2.57 (0681) mmol) and (bromomethyl)cyclopentane (335 mg, 2.05 mmol). The reaction was stirred at 65C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC- MS to yield 7-(cyclopentylmethyl)-3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one 210 mg (47%). (0682) 1H NMR (DMSO-de, 400 MHz): delta 7.53 (s, 1 H), 7.51 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.69 (d, J = 7.6 Hz, 2H), 2.29-2.24 (m, 2H), 1.58-1.45 (m, 6H), 1.22-1.19 (m, 2H), 1.00- 0.89 (m, 4H). (0683) LC-MS: {m/z) 258.2 (MH+) tR (minutes, method 3) = 2.24 minutes

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; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1003-99-2

2-Bromo-5-fluoro-N-(propan-2-yl)aniline E-1.7″” ‘ 2-bromo-5-fluoroaniline E-1.7″”” (2.00 g; 10.53 mmol) is suspended in 20 ml DCM and propan-2-one (1.55 ml; 21.05) is added and the reaction mixture is stirred for 16 at 20°C. Afterwards sodium triacetoxyborohydride (4.69 g; 21.05 mmol) is added and the reaction mixture is stirred for 48h at 20 °C. The reaction mixture is poured into water and extracted with DCM. The combined organic layer is dried over MgS04 the solid materials are filtered off and HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. The crude product is purified using reversed phase chromatography (Method: prep. HPLC1). Product containing fractions are combined and extracted with DCM. To the organic layer HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. Yield 91percent (2.57 g; 9.58 mmol) HPLC-MS: tRet = 1.09 min; method VAB

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1003-99-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary