Category: bromides-buliding-blocks

Reference of 103-64-0,Some common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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 thiophenols (0.5 mmol), 1-((E)-2-iodovinyl)benzenes (0.6 mmol), CuI (19 mg, 20 mol %), L5 (19 mg, 20 mol %), and Cs2CO3 (326 mg, 2 equiv) in DMSO (3 mL) was stirred in N2 at 100 C for 24 h., The mixture was quenched with saturated salt water (10 mL) after the reaction completion. The solution was extracted with ethyl acetate (3×10 mL). The organic layers were combined and dried by sodium sulfate. The product 2-(styrylthio)phenols was obtained by flash column chromatography on silica gel.

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

Reference:
Article; Xu, Run-Sheng; Yue, Lei; Pan, Yuan-Jiang; Tetrahedron; vol. 68; 25; (2012); p. 5046 – 5052;,
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Synthetic Route of 1347736-74-6, 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. 1347736-74-6, name is 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

the 4,6-dibromo-5-fluorobenzo [c] [1, 2, 5] thiadiazole (2.00g, 6 . 41 mmol) and ethanol (50 ml) is added to the three-hole and round-bottom flask cooled to 0 C. In slowly adding Na[BH4] (4.6g, 0 . 12 mol) later, the reaction mixture is stirred at room temperature overnight. After removing the volatile substance, the 100 distilled water added to the reaction mixture, then the mixture is extracted with ethyl ether, salt water cleaning, and the anhydrous Na2SO4dry. Removing volatile substances from the extract to obtain a light brown powder A (1.20g, 66%).

The synthetic route of 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SABIC Global Technology Company; Ibrahim Lafia, S·M·; Tate, C. Haug; Gillian, M · Bristol Senanayake; Amit, K · Jiefudiya; Ahmed, I. Abdul Rahman; (26 pag.)CN105531280; (2016); A;,
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Synthetic Route of 52723-82-7, These common heterocyclic compound, 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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.

A solution of 4-bromo-5-fluoro-2-methylaniline (10.2 g, 50 mmol) and 3- chlorobenzenecarboperoxoic acid (34.5 g, 200 mmol) in DCE (10 mL) was stirred under nitrogen at reflux for 2 hours. After cooling to rt, the mixture was dispersed between DCM and saturated aqueous Na2S03 solution. The organic layer was collected, concentrated to dryness and purified by flash column chromatography to give the title compound as a brown oil (7.02 g, 60.0percent yield).

The synthetic route of 52723-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
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Reference of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Under nitrogen atmosphere, 3-bromo-2-methylaniline (5.01g, 26.9 mmol) was dissolved in DCM (100 mL). To this solution, cooled with ice bath, TEA (7.5 mL, 53.9 mmol) and 4-tert-butylbenzoyl chloride (5.3 g, 26.9 mmol) were added dropwise and stirred at 0 C for 4 h. The reaction mixture was diluted with DCM (100 mL), washed with water (2×30 mL), 1N hydrochloric acid solution (30 mL), saturated sodium hydrogen carbonate solution (30 mL) and brine (30 mL), then the organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was suspended in hexane, then the precipitate was collected by filtration, washed with hexane then dried to afford N-(3-bromo-2-methylphenyl)-4-(tert-butyl)benzamide (9.0 g). 1H NMR (400 MHz, DMSO-d6) delta 10.06 (s, 1H), 7.92 (d, J = 8.4 Hz, 2H), 7.54 (m, 3H), 7.33 (d, J = 7.7 Hz, 1H), 7.18 (t, J = 8.0 Hz, 1H), 2.27 (s, 3H), 1.32 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; Carna Biosciences, Inc.; KAWAHATA, Wataru; ASAMI, Tokiko; SAWA, Masaaki; ASAMITSU, Yuko; IRIE, Takayuki; MIYAKE, Takahiro; KIYOI, Takao; EP2824099; (2015); A1;,
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Related Products of 327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

[0141] Into a 100 mL three- necked flask were added 4.62 g 1- bromo- 2, 4, 5- trifluorobenzene (0.022 mol) andanhydrous tetrahydrofuran (50 mL) . The resulting mixture was cooled to- 20 C. The solution of isopropylmagnesiumbromide (22 mmol) in tetrahydrofuran (22 ml, 1 M THF) was slowly added dropwise under nitrogen. After the additionwas complete, the reactants were maintained at- 20 C for later use.[0142] Cuprous bromide – dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. Theresulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (2.81 g, 0.015 mol)in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammoniachloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separatedwater layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together andfurther washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed byfiltration and concentration to obtain a crude product, which was further treated by column chromatography to obtain acompound (3.69 g, 0.0115 mol, yield 77%).1H NMR (500 MHz, CDCl3) delta 7.05 (d, J = 8.3 Hz, 1 H), 6.91 (d, J = 6.6 Hz, 1 H), 4.56 (d, J = 9.0 Hz, 1H), 4.13?3.96 (m,1 H), 3.68 (d, J = 6.0 Hz, 2H), 2.85?2.65 (m, 2H), 1.86 (dd, J = 12.4, 7.7 Hz, 1H), 1.68 (s, 1H), 1.42 (s, 9H). Ms (M++1): 320.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Hisoar Pharmaceutical Co., Ltd; PAN, Xianhua; LI, Weijin; ZHANG, Qunhui; RUAN, Libo; YU, Wansheng; DENG, Fei; MA, Tianhua; HUANG, Mingwang; HE, Minhuan; EP2647624; (2013); 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 185122-74-1 as follows. Computed Properties of C9H10BrN

At 0 0C and under protective atmosphere, a solution of 2-Propanesulfonyl chloride (1 1.87 ml_, 121 mmol) in DCM (121 ml.) was added gradually to a solution of 5-bromo-2,3- dihydro-1 H-inden-1 -amine (12.8 g, 60.4 mmol) and 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (4.83 ml_, 32.1 mmol) in Dichloromethane (300 ml_). The reaction was stirred at rt overnight. The reaction mixture was washed with 1 N KHSO4 (1x) and sat NaHCObeta (2x) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in heptane) afforded the title compound as a white solid.(6.0 g, 31 %). MS (ESI) : m/z [M – H]” 317.0

According to the analysis of related databases, 185122-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. Organon; GILLEN, Kevin James; GILLESPIE, Jonathan; JAMIESON, Craig; MACLEAN, John Kinnaird Ferguson; MOIR, Elizabeth Margaret; RANKOVIC, Zoran; WO2010/115952; (2010); A1;,
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Synthetic Route of 43204-63-3, A common heterocyclic compound, 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, molecular formula is C4H10Br3N, 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.

Add 5-amino-3,4-dihydroquinolin-2(1H)one 7 (5.00 g, 30.83 mmol) to 40 ml of water in turn, di-(2-bromoethyl)amine hydrobromide (50.57 g, 33.91 mmol), stirring to 80 C, An aqueous solution of potassium hydroxide (1.90 g, 33.91 mmol, 10 ml) was added dropwise in three portions over half an hour. After the addition is completed, the reaction is heated to 100 C. The reaction was further incubated for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was adjusted to pH 10 with a 10% aqueous potassium hydroxide solution to precipitate a large white solid. Filtered, washed with a suitable amount of water, dried to give a white powdery solid 8 (6.4 g, yield 61%, Mp 235-237 C);

The synthetic route of 43204-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Ji Qinggang; Deng Qiao; (15 pag.)CN109438344; (2019); A;,
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Related Products of 21524-34-5, 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 21524-34-5 as follows.

EXAMPLE TEN: Synthesis of Ligand 7; An oven-dried three-neck 250 mL round bottom flask, which was equipped with a magnetic stir bar and charged with magnesium shavings (559 mg, 24.3 mmol), was fitted with a reflux condenser, addition funnel, and glass stopper. The flask was purged with argon and then THF (15 mL) and 2,4,6-triisopropylbromobenzene (2.83 g, 10 mmol) were added via syringe. The reaction mixture was heated to reflux and 1 ,2-dibromethane (40 uL) was added via syringe. The reaction was allowed to stir at reflux for 1 h and then the addition funnel, which was charged with l,2-dibromo-3,4,5,6-tetramethylbenzene (2.92 g, 10 mmol) in 40 mL of THF, was opened and the solution was added over a 1 h period. The mixture was stirred for 5 h at reflux and then cooled to room temperature where CuCl (1.0 g, 10 mmol) was added quickly to the reaction mixture. Next, ClPCy2 (2.65 mL, 10 mmol) was then added in a dropwise fashion and the reaction mixture was heated to 75 0C for 60 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc, washed 3 times with 30% NH4OH, dried over MgSO4, and concentrated under reduced pressure. The crude material was recrystallized from benzene to yield the product as a white solid (1.507 g, 28% yield). 1H NMR (300 MHz, CDCl3) delta: 7.36 (s, 5H), 7.15 (s, 2H), 2.99 (septet, J= 7.0 Hz, IH), 2.44 (s, 3H), 2.35-2.14 (m, HH), 1.98 (s, 2H), 1.80-1.44 (m, 14H), 1.39-1.04 (m, 22H), 0.91 (d, J= 6.5 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) delta: 150.9, 145.8, 145.4, 144.6, 140.0, 138.5, 135.8, 135.6, 135.5, 135.5, 128.6, 124.3, 40.2, 39.9, 35.4, 35.2, 34.5, 30.7, 29.5, 27.8, 27.7, 27.4, 27.2, 25.9, 25.0, 24.6, 21.2, 20.8, 17.7, 17.3 ppm (Observed complexity is due to P-C splitting). 31P NMR (121 MHz, CDCl3) delta: 16.33 ppm.

According to the analysis of related databases, 21524-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
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These common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-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. category: bromides-buliding-blocks

5-Bromo-2-fluoroaniline (2.85 g, 15.00 mmol) and 4-methylmorpholine (1.65 mL, 15.00 mmol) were dissolved in anhydrous dichloromethane (20 mL) and the solution was cooled to -20 C. Add compound 5 (3.55 g, obtained in the synthesis of steps 1-3,13.66 mol), the mixture was slowly warmed to 20 C and kept stirring at 20 C for 12 hours. The resulting red suspension was poured into water (80 mL). The phases were separated and the organic layer was dried with Na2SO4, filtered and evaporated.A red oil was obtained and the residual red oil was dissolved in methanol (20 mL).The solution was heated to reflux for 1 hour to form a precipitate. The mixture was cooled to 4 C.The precipitate was collected by filtration, washed with methanol and dried to give a pale pink solid.N-(5-Bromo-2-fluorophenyl)-6-(furan-2-yloxy)pyridine-3-sulfonamide (Compound 6), 3.50 g, yield 62%.

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

Reference:
Patent; Dou Yuling; (11 pag.)CN108484585; (2018); A;,
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Synthetic Route of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

The 5.018 (0.02 muM) 3, 5 – dibromoaniline and 9.350 g (0.05 muM) (6 – aminonaphthalen – 2 – yl) boronic acid is added to a 500 ml three-neck bottle in, adding 400 ml tetrahydrofuran (THF), then adding 2 mol/L potassium carbonate solution of 75 ml, and add 0.5 ml of aliquat 336, magnetic stirring and open the argon gas, oil bath is heated to 75 C after, adding 0.020 g […] palladium, reflux reaction 24 h, the reaction liquid is poured into the water in the, a large amount of precipitate out. For funnel, evaporating the solvent under reduced pressure. The product in order to dichloromethane: hexane=3:1 ([…]) as the mobile phase silica gel as stationary phase makes the column chromatographic purification, collecting products and turns on lathe does, in 90 C drying in vacuum 24 h, to obtain the target product 5.632 g, yield is 75%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromoaniline, its application will become more common.

Reference:
Patent; Hunan University of Technology; Ding Qian; Tan Jinghua; Liu Yiwu; Fu Hao; (20 pag.)CN109053466; (2018); A;,
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