Tag: M.W=100-200

Synthetic Route of 58534-95-5,Some common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-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.

The mixture of 12 (30 g), 13 (60 g), K2CO3 (91 g) and Pd(dppf)2Cl2 (19.25 g) in solvent (dioxane 400 mL, H2O 100 mL) was purged with argon in a pressure vessel for 5 min and stirred for 15 h at 100 C. The solvent was removed under reduced pressure and the remaining residue was purified by flash column chromatography. The purified material was then dissolved in MeOH and treated with HCl/MeOH. The solvent was removed and the remaining solid was washed with IPA-heptane (1/1) to afford 14.

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-fluoroaniline, its application will become more common.

Reference:
Patent; Achillion Pharmaceuticals, Inc.; Gadhachanda, Venkat Rao; Pais, Godwin; Hashimoto, Akihiro; Wang, Qiuping; Chen, Dawei; Wang, Xiangzhu; Agarwal, Atul; Deshpande, Milind; Phadke, Avinash S.; Wiles, Jason Allan; US2015/239920; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10485-09-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 10485-09-3 name is 2-Bromoindene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a 200 mL reactor sufficiently dried and purged with argon, 0.98 g (40.3 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a reflux condenser was attached, and a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. A 10 mL diluted solution of 1.95 g (10.0 mmol) of 2-bromoindene is added dropwise (1.0 mL after addition, followed by heating to reflux until the color of iodine disappears with a drier, remaining after dropping of the reaction drop) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 6.00 mL (50.2 mmol) of dimethylsilyl dichloride in 10 mL of n-hexane diluted solution,The reaction was slowly added at -78 C with cooling, and stirring was continued for 19 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 20 mL of tetrahydrofuran and 1.00 mL (10.6 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue. 2.65 g (10.0 mmol) of 7- (4-trimethylsilylphenyl) idene synthesized by the method described in WO2012 / 133717 in a fully dried, argon-substituted 100 mL reactor.15 mL of tetrahydrofuran was charged, 6.45 mL (hexane solution, 1.55 M, 10.0 mmol) of n-butyllithium solution was added, and the mixture was stirred at room temperature for 2 hours. This solution was added dropwise to the previously diluted reaction residue diluted solution cooled to -78 C., and stirring was continued for 3 hours while slowly returning to room temperature. Saturated aqueous ammonium chloride solution was added, the solubles were extracted with n-hexane, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the target compound represented by the following formula (A-1 L)Compound (A-1L) was obtained as an isomer mixture of 2.12 g (yield 48%).

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

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 586-61-8, These common heterocyclic compound, 586-61-8, name is 1-Bromo-4-isopropylbenzene, 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 6-methoxy-3,4-dihydronaphthalen-l(2H)-one L31-1 (5 g, 28.41 mmol) in xylene (125 mL) was added l-bromo-4-isopropylbenzene (6.78 g, 34.07 mmol) followed by cesium carbonate (32.4 g, 99.41 mmol) and degassed with argon for 15 min in a sealed tube. To the resulting solution was added Pd(OAc)2(636 mg, 2.839 mmol) and Xanthphos (2.5 g, 4.251 mmol) and degassing was continued for another 15 min. Then the reaction mixture was sealed properly and heated to l30C for 24 h. After completion of the reaction (monitored by TLC and LCMS), the reaction mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The resulting crude compound was purified by silica gel column chromatography eluting with 0-10% ethyl acetate in -hexane to afford 2.5 g (30% yield) of compound L31-2 as brown oil.LCMS-Condition-1 : [M + H]+= 295.05; Rt = 2.22 min?H NMR (400 MHz, DMSO-ifc) d: 7.87 (d, J= 8.31 Hz, 1H), 7.15-7.20 (m, 2H), 7.08 (d, J = 8.31 Hz, 2H), 6.89-6.94 (m, 2H), 3.84 (s, 3H), 3.80 (dd, = 4.89, 11.25 Hz, 1H), 3.02-3.13 (m, 1H), 2.82-2.98 (m, 2H), 2.20-2.36 (m, 2H), 1.20 (d, J= 6.85 Hz, 6H).

Statistics shows that 1-Bromo-4-isopropylbenzene is playing an increasingly important role. we look forward to future research findings about 586-61-8.

Reference:
Patent; RADIUS PHARMACEUTICALS, INC.; MILLER, Chris; (188 pag.)WO2019/144132; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 32046-62-1, 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. 32046-62-1, name is 5-Bromo-1H-benzotriazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A flask equipped with a stirring bar and flushed with Ar is loaded with 5- bromo-1 – -benzotriazole (200 mg; 1.01 mmol; 1 eq.), potassium iodide (17 mg; 0.10 mmol; 0.10 eq.), potassium carbonate (698 mg; 5.05 mmol; 5 eq.) and acetone (20 ml_). The mixture is cooled in an ice bath and iodomethane (0.08 mL; 1.11 mmol; 1.10 eq.) is added via syringe. After 15 minutes, the bath is removed and the mixture is stirred for 48 h at room temperature. The reaction mixture is then filtered, and the filtrate is evaporated in vacuo. The residue is purified by FCC (0-30% EtOAc gradient in hexane) to provide two regioisomers: 5-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (79, 63 mg, 0.30 mmol, 29%; UPLC purity: 100%). 6-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (80, 57 mg, 0.27 mmol, 27%; UPLC purity: 100%).

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-1H-benzotriazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2,4-difluorobenzene

Method A: A suspension of Mg turnings (3.47 g, 143 mmol) in THF (250 mL) was heated to 35 °C under nitrogen. A portion of 1-bromo-2,4-difluorobenzene (1 mL, 8.85 mmol) was added to the reactor, and the resulting mixture was heated at 35 °C for 30 mm to initiate thereaction. The reaction mixture was cooled to 30 °C, and the remainder of 1-bromo-2,4- difluorobenzene (16.4 mL, 145.15 mmol) was added to the reactor at 28?32 °C over 30 mm. The reaction was stirred at 30 °C for 2 h, at which point complete consumption of Mg was observed. The reaction was cooled to less than 0 °C, and a solution of ethyl 2-(5-(4- cyanophenoxy)pyridin-2-yl)-2,2-difluoroacetate (III) (35 g, 110 mmol) in THF (100 mL) wasadded at less than 5 °C over 30 mm. The reaction was stirred at 0 °C for 1 h and quenched into a 2 N HC1 solution (150 mL) at less than 10 °C (pH = 1?2). The reaction was stirred at 20 °C for 18 h, at which point HPLC analysis indicated that there was still about 10percent of hemiketal intermediate (ha) remaining. It was further stirred at 30 °C for 5 h, at which point HPLC analysis indicated that the hemiketal (ha) intermediate was fully consumed. The layerswere separated, and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with a sat. NaHCO3 solution (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated to give a light tan solid (45.6 g). The solid was dissolved in EtOAc (60 mL) at 60 °C, and heptane (100 mL) was added. The mixture was seeded and stirred at 20 °C for 18 h to afford a suspension. The suspension was filtered and the solid was dried to afford the desired product as a white solid (25.5 g). The filtrate was concentrated andrecrystallized from MTBE (50 mL) and heptane (100 mL) to give a light brown solid (14.1 g)after drying, affording a combined yield of 90percent. ?H NMR (400 MHz, CDC13) 8.37 (d, J =2.7 Hz, 1H), 8.08 (td, J = 8.4, 6.4 Hz, 1H), 7.87 (d, J = 8.6 Hz, 1H), 7.75 ? 7.66 (m, 2H), 7.54(dd, J= 8.6, 2.8 Hz, 1H), 7.17?7.08 (m, 2H), 7.01 (dddd, J= 8.6, 7.6, 2.5, 0.9 Hz, 1H), 6.84 (ddd, J= 11.0, 8.6, 2.4 Hz, 1H); ESIMS m/z 387.0 ([M+Hj).

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; VIAMET PHARMACEUTICALS, INC.; YANG, Qiang; HAO, Yan; RYAN, Sarah; WHITEKER, Gregory; (26 pag.)WO2017/87643; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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. name: 1-Bromo-2,2-dimethylpropane

1-neopentyl-4-(4-nitrophenyl)-1H-imidazole To a solution of 4-(4-nitrophenyl)-1H-imidazole (0.500 g, 2.64 mmol) in N,N-dimethylformamide (10 ml) was added cesium carbonate (1.292 g, 3.96 mmol) followed by 1-bromo-2,2-dimethylpropane (0.366 ml, 2.91 mmol). After heating at 850 overnight, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Normal phase chromatography provided the title compound.

The synthetic route of 1-Bromo-2,2-dimethylpropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Hansen, Todd M.; Longenecker, Kenton; Heyman, Howard R.; Curtin, Michael L.; Clark, Richard F.; Sorensen, Bryan; Ji, Zhiqin; Woller, Kevin; Doherty, George; Frey, Robin; (246 pag.)US2017/65575; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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. Formula: C7H6BrF

l-Bromo-3-fluoro-5-methylbenzene (5.00 g, 26.5 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78 C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 16.2 mL, 29.1 mmol) was added. After stirring at -78 C for 30 min, N,N-dimethylformamide (2.32 g, 31.7 mmol) was added. After stirring at -78 C for an additional 15 min, acetic acid (6 mL) and water (100 mL) was added and the mixture was warmed to RT. After extraction with ethyl acetate, the organic phase was washed with 1 M hydrochloride acid solution and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (5.45 g, 95% of theory). GC-MS (Method 1G): Rt = 4.39 min, MS (ESIPos): m/z = 217 [M+H]+

The synthetic route of 1-Bromo-3-fluoro-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; CANCHO-GRANDE, Yolanda; BEYER, Kristin; ROeHRIG, Susanne; KOeLLNBERGER, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; WO2015/67549; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-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.

To a stirred solution of 3-bromo-5-methylaniline (504 mg, 2.68 mmol), 2-fluorophenyl boronic acid (413 mg, 2.95 mmol) and potassium carbonate (1.1 g, 8.04 mmol) in a mixture of DMF (15 mL) and water (5.0 mL) was added tetrakis(triphenylphosphine)palladium(0) (155 mg, 0.13 mmol) at RT. The reaction mixture was evacuated, flushed with nitrogen and stirred at 80 C for 16 h. The reaction mixture was cooled to RT, diluted with ethyl acetate (30 mL), washed with water (30 mL) and brine (30 mL). The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 400 mg of the titled product. 1H NMR (300 MHz, DMSO-d6) delta 2.18 (s, 3H), 5.07 (s, 2H), 6.38-6.51 (m, 3H), 7.18-7.25 (m, 2H), 7.30-7.41 (m, 2H); APCI-MS (m/z) 202 (M+H)+.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Dnyaneshwar Eknath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (93 pag.)WO2017/37595; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, HPLC of Formula: C7H8BrN

2. Synthesis of 1-(6-bromo-1H-indazol-1-yl)ethanone Into a 500 mL round-bottom flask, was placed a solution of 5-bromo-2-methylbenzenamine (25 g, 134.41 mmol) in CHCl3 (60 mL). To the above was added acetic anhydride (27.97 g, 273.95 mmol) dropwise with stirring, while cooling to a temperature of 0 C. over a time period of 1 hour. The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at 0-5 C. in a bath of H2O/ice. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). Addition of isoamylnitrite (37.35 g, 319.23 mmol) was next. This was followed by the addition of KOAc (4.39 g, 44.80 mmol). To the mixture was added acetic anhydride (47.6 g, 466.21 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. Adjustment of the pH to 7 was accomplished by the addition of NaHCO3 (50%). The resulting solution was extracted three times with 600 mL of ethyl acetate and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 ethyl acetate/petroleum ether solvent system. This resulted in 26 g (81%) of 1-(6-bromo-1H-indazol-1-yl)ethanone as a orange solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/200471; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 17247-58-4, The chemical industry reduces the impact on the environment during synthesis 17247-58-4, name is (Bromomethyl)cyclobutane, I believe this compound will play a more active role in future production and life.

Step 2: (3aS,4S,65′)-2-[(1S)-1-chloro-2-cyclobutylethyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole (intermediate 2)To Mg (13.60 g, 560 mmol) in THF (650 mL) was added DIBAL (1 M in toluene, 9.1 mL, 9.1 mmol) under N2, and the mixture was stirred for 30 min at room temperature. Intermediate 2 (40.6 mL, 360 mmol) was then added dropwise below 40 C. and the reaction mixture was stirred at room temperature for 2.5 h. After cooling to -78 C., the solution was transferred to a solution of intermediate 1 (70 g, 0.267 mol) in THF (400 mL) at -78 C. under N2 protection and the resulting mixture was stirred for 45 min. ZnCl2 (1 M in Et2O, 750 mL, 750 mmol) was then added in one portion, the mixture was allowed to warm to room temperature and stirred overnight. To the reaction mixture were added ethyl acetate (800 mL) and sat. NH4Cl (350 mL), the mixture was stirred for 1 h and the organic layer was washed with water (300 mL), brine (300 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate=20:12:1) to afford intermediate 2 (65 g, 82% yield) as a colorless oil.

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, (Bromomethyl)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2010/81633; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary