Tag: M.W=200-300

Electric Literature of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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.

Freshly crystalized BS (13.84 g, 77.80 mmol, 1.2 eq) was added to the solution of 1- bromo-4-methylnaphthalene (15.0 g, 67.84 mmol, 1.0 eq) and AIBN (1.11 g, 6.78 mmol, 0.1 eq) in carbon tetrachloride (150 mL) and the mixture was stirred at 80 C for 16 h under nitrogen atmosphere. After complete consumption of starting material, water was added to the reaction mixture and extracted with DCM. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulfate, filtered, and the solvent evaporated from the filtrated under reduced pressure to obtain l-bromo-4-(bromomethyl)naphthalene. LCMS: Purity 96.83%

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-4-methylnaphthalene, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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 B: 3-(2.2-Difluoro-benzo? .31dioxol-5-ylmethyl)-pyrrolidine-1 – carboxylic acid tert-butyl ester. A stream of N2 was bubbled through neat 3- methylene pyrrolidine-1 -carboxylic acid te/t-butyl ester (792 mg, 4.33 mmol) for 15 min before charging the flask with 9-BBN (0.5 M in THF, 8.8 ml_). The reaction mixture was heated at reflux for 2.5 h; then cooled to rt. The resultant mixture was then added, via cannula, to a preformed solution consisting of 5-bromo-2,2-difluoro-1 ,3-benzodioxole (1.01 g, 4.24 mmol), Pd(dppf)CI2»CH2CI2 (92 mg), and potassium carbonate (760 mg, 5.50 mmol) in DMF/H2O (10 mL/1 ml_). The reaction mixture was heated at 60 0C for 18 h, cooled to rt and poured into water. The pH of the mixture was adjusted to 11 with NaOH (1 N), and extracted with EtOAc (3x). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (1.4 g, 94%).

The synthetic route of 33070-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, Guy, J.; TICHENOR, Mark, S.; MERIT, Jeffrey, E.; HAWRYLUK, Natalie, A.; CHAMBERS, Alison, L.; KEITH, John, M.; WO2010/141809; (2010); A1;,
Bromide – Wikipedia,
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Reference of 937046-98-5, A common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

7-Bromo-pyrrolo[2,1-f]triazine-4-ylamine 3 (2.78 gm, 1.1 equiv 13.2 mmol, prepared according to WO2007056170) was suspended in anhydrous THF (70 mL). Under inert atmosphere, 1,1,4,4-tetramethyl-1,4-dichlorodisilyethylene (2.83 gm, 1,1 equiv, 13.2 mmol) was added along with sodium hydride (1.05 gm, 26.3 mmol, 2.2 equiv) was added and the mixture was stirred for 20 min at room temperature. The reaction was then cooled to -78 C before n-BuLi (27.4 mL, 43.89 mmol, 1.6 M in Hexanes) slowly over 5 min. The reaction was allowed to stir for a further 15 min before lactone 4 (dissolved in 3 mL was added dropwise). When the reaction was complete by LCMS, the reaction was quenched with acetic acid. The reaction was concentrated in vacuo before being diluted in EtOAc and washing with water, saturated NH4Cl and brine. The organic layers were dried over MgSO4, filtered and concentrated in vacuo. The material was purified by silica chromatography (0-50% EtOAc/Hexanes) provided a 3:1 mixture of 5 anomers. 4.38 gm (y. 60%) of a white solid was obtained.1H NMR (400 MHz) (CD3)2CO 8.00 (s, 1H), 7.30-7.47 (m, 15H), 7.20 (d, 8.4 Hz, 1H), 6.87 (d, 8.4 Hz, 1H), 5.40 (d, 8.2 Hz, 1H), 4.65-4.4.0 (m, 3 H), 3.65 (dd, 8.8, 4.3.2, 1 H), 3.55 (dd, 8.8, 4.3.2, 1 H) LC-MS (m/z 553.01, M+H+).

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Metobo, Sammy E.; Xu, Jie; Saunders, Oliver L.; Butler, Thomas; Aktoudianakis, Evangelos; Cho, Aesop; Kim, Choung U.; Tetrahedron Letters; vol. 53; 5; (2012); p. 484 – 486;,
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. 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,4-Dibromo-2,3-difluorobenzene

To a solution of R-43c (1.29 mL, 10 mmol) in THF (5 mL) at -40 C. was added the iso-PrMgCl.LiCl solution (5.5 mL, 11 mmol, 2.0M in THF) at a rate that maintained the reaction temperature below -30 C. Stirring was continued at -35 to -30 C. for 1 h then warmed to -7 C. for an additional 1 h. The reaction mixture was cooled to -30 C. and DMF (1.00 mL, 13 mmol) was added in one portion (temperature rose to -23 C.) and stirring continued for 3.5 h at -25 to +15 C. The reaction mixture was poured into 1M H2SO4 and ice and the resulting mixture was saturated with solid NaCl and twice extracted with MTBE. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 2.17 g (98%) of R-43d as a white solid.

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; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene, 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 328-70-1, Application In Synthesis of 1-Bromo-3,5-bis(trifluoromethyl)benzene

A 250 ml round-bottom flask was charged with magnesium (turnings; 2.18 g; 89.5 mmol), and argonated. Then, Et2O (60 ml), I2 (one crystal) were added, and a solution of 1-bromo-3,5-bis(trifluoromethyl)benzene (26.67 g; 91.0 mmol) in Et2O (60 ml) was added portionwise over 45 min with stirring. After 2 h the mixture was cooled with ice-water bath and AsCl3 (2.2ml; 26.1 mmol) was added dropwise, that caused formation of crystalline precipitate. Stirring was continued at RT for 16 h, and aqueous NH4Cl (100 ml; 10%) was added. The resulted mixture was extracted with ethyl acetate (3 100 ml), and combined organic phases were washed with brine (100 ml), and dried over MgSO4. The mixture was filtered, evaporated, and residue grey-brownish solid was crystallized from n-hexane (dissolved in boiling solvent and slowly cooled to ca. 0 C; 30 ml) to obtain 8d (17.99 g; 25.18 mmol; 97%) as white solid.

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Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
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Related Products of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-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.

To a solution of 100 g of this 2-iodo-7-propyl-9,10-dihydrophenanthrene in 300 mL of THF was added 3.3 g of tetrakis(triphenylphosphine)palladium (0) and the mixture was stirred at room temperature. This mixture was then reacted with a Grignard reagent prepared from 79 g of 3,4,5-trifluorobromobenzene and 9.1 g of magnesium. Following stirring for 2 hours at room temperature, the mixture was allowed to cool to room temperature, water was added, the product was extracted into toluene, and the organic layer was washed sequentially with water and a saturated aqueous solution of sodium chloride before being dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel columnchromatography (hexane) and then recrystallized 3 times from ethanol to yield 45 g of white crystals of 2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene. Measurement of the phase transition temperature revealed a transition from the crystalline phase to an isotropic liquid phase at 68C under rising temperature conditions. NMR: delta = 0.99 (t, J=7Hz, 3H), delta = 1.65 (m, 2H), delta = 2.52 (t, J=7Hz, 2H), delta = 2.88 (s, 4H), delta = 6.9 to 7.6 (m, 8H), MS: m/e = 352 (M+)

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; DAINIPPON INK AND CHEMICALS, INC.; EP1201632; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, 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. HPLC of Formula: C7H6Br2

To a solution of 1 , 3-dibromo-2-methylbenzene (3 g, 12.00 mmol) in Tetrahydrofuran (THF) (100 mL) stirred under nitrogen at -78 C was added BuLi (9.00 mL, 14.40 mmol) dropwise. The reaction mixture was stirred at -78 C for 20 min. DMF (1.1 15 mL, 14.40 mmol) was added dropwise. The reaction mixture was continuously stirred for 2 hours. The reaction was quenched with sat. aq. ammonia chloride solution. The aqueous layers were seperated and extracted by EA for 3 times. The combined organic layers were washed by brine, dried over anhydrous sodium sulfate. The dried solution was concentrated in vacuo to afford 3-bromo-2-methylbenzaldehyde (D93) (2.4g), which was used for the next step without further purification. MS (ES):C8H7BrO requires 197.9; found 199 (M+H+)

The synthetic route of 2,6-Dibromotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
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Application of 960203-41-2, A common heterocyclic compound, 960203-41-2, name is (2-Bromophenyl)(2,4-dimethylphenyl)sulfane, molecular formula is C14H13BrS, 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.

2.1 g of the compound C synthesized in Example 1 was charged into a 100 mL three-necked flask, and 0.9 g of piperazine, 0.3 g of cuprous iodide, 0.5 g of 2-acetylcyclohexanone and 3.0 g of potassium carbonate of 100 to 200 mesh were weighed into a flask, The amount of 50mL DMF into the flask,The reaction mixture was heated to reflux. TLC was used to detect the reaction. The reaction was complete with 100 mL of ethyl acetate and 150 mL of water. The filtrate was separated by suction filtration and the organic phase was washed twice with 100 mL of water. The organic phase was washed with anhydrous sulfuric acid After drying for 2 h, the oil was concentrated at 45 ° C to obtain an oil. After 30 mL of n-hexane was added to the oil, the mixture was stirred and crystallized for 3 h. After filtration, the filter cake was washed twice with a little solvent and the cake was vacuum dried at 40 ° C for 12 h. Brown solid product 2.2 g, yield 81.5percent.

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; Beijing Wanquan German public medicine Biotechnology Co., Ltd; Xu, Yong; Zhao, Guolei; (6 pag.)CN105367516; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 4263-52-9, name is Sodium 2-bromoethanesulphonate, A new synthetic method of this compound is introduced below., HPLC of Formula: C2H4BrNaO3S

44.6 g of isophorone diisocyanate (IPDI) was added in a mechanically agitated round-bottom flask. 0.2 mL of catalyst dibutyltin dilaurate was added in the IPDI, and 17.8 g of dimethyl ethanolamine (HO CH2CH2N(CH3)2) was added dropwise in the IPDI while stirring at 30 C. using a dropping funnel to form a reaction mixture. The reaction mixture reacted for 1 hr, and then was stirred to react for 12 hrs at 30 C. 42.2 g of 2-bromoethyl sodium sulfonate which was dissolved in 400 mL of anhydrous tetrahydrofuran was added dropwise in the reaction mixture and reacted for 1 hr to yield a white precipitate. The white precipitate was centrifugalized several times to yield the isocyanate-terminated betaine compound.

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; Shenzhen University; CHEN, Shiguo; YUAN, Lingjun; ZHU, Xingli; CHEN, Shaojun; GE, Zaochuan; (11 pag.)US2017/339960; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 327-51-5, These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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.

Example i-7: methyl 5-fluoro-2-methoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxa borolan-2-yl)benzoate (i-7)Scheme i-7.i-7 i) Preparation of 4-bromo-2,5-difluorobenzoic acid (i-7b)To a solution of l,4-dibromo-2,5-difluorobenzene (i-7a) (1.1 g , 4 mmol) in Et20 (10 mL) at – 78 C was added n-BuLi (2.5M in hexane, 1.6 mL, 4 mmol) dropwise. The mixture was stirred for 30 min at -78 C and then quenched with an excess of freshly crushed dry ice. After 15 min, the mixture was brought to rt and diluted with H20. The aqueous layer was separated, and the organic layer was extracted with 10% aq. Na2C03. The combined aqueous layers were acidified with 1M HC1 and extracted with EtOAc. The combined organic layers were dried with Na2S04 and concentrated to give the title compound. LCMS (ESI) calc’d for C7H3BrF202 [M+H]+: 237, found: 237

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; N.V. ORGANON; KARSTENS, Willem Frederik Johan; STELT, Mario van der; CALS, Jos; AZEVEDO, Rita Corte Real Goncalves; BARR, Kenneth Jay; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; DUAN, Xiaobang; WO2012/106995; (2012); A1;,
Bromide – Wikipedia,
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