Category: bromides-buliding-blocks

61613-22-7, A common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, molecular formula is C12H10BrN, 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) To a solution of 150 mL of a 0.194 mol/L 2-bromo-N-phenylaniline in anhydrous tetrahydrofuran at a temperature of -78 C, 2.5 mL/L of n-BuLi hexane solution 25.6 mL was added dropwise. After stirring for 2 h, 110 mmol of fluorenone was added, and after stirring for 30 min, the reaction mixture was warmed to room temperature and stirred overnight; after quenching with a large amount of water, the mixture was extracted three times with chloroform; and the combined chloroform solution was dried over anhydrous magnesium sulfate. Concentration, filtration and evaporation gave the crude hydroxy intermediate; the obtained crude hydroxy intermediate was dissolved in 150 mL of chloroform, 64.02 mmol of methanesulfonic acid was added, then refluxed for 10 hours; after cooling to room temperature, the resulting solution was carefully poured into excess carbonic acid. The mixture was stirred with chloroform for 20 min; EtOAc (EtOAc)EtOAc. -] (See Li, B.-W.; Li, Z.-Y.; Hu, T.-P.; Zhang, Y.; Wang, Y.; Yi, Y.-P.; Guo, F .-Y.;Zhao, L.-CJ Mater. Chem. C, 2018, 6, 2351-2359).The yield of the obtained 10H-spiro[acridine-9,9′-oxime] was 51%, and the purity was >99%.

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shihezi University; He Lin; Wang Weihua; Du Guangfen; Gu Chengzhi; (22 pag.)CN109485605; (2019); A;,
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Some common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, molecular formula is C6H2Br2F2, 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. 28342-75-8

100 g of intermediate 1-1, 186 g of intermediate 1-2, 203 g of potassium carbonate, 23.7 g of tetrabutylammonium bromide (TBAB) were added to a 2 L three-necked flask, and 800 ml of toluene, 200 ml of ethanol, and 200 ml of water were sequentially added. Nitrogen gas was introduced, stirred for 15 min, 2.1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated to 80 ¡ãC for refluxing for 8 h. TLC was used to monitor the reaction of the starting material to room temperature and filtered to remove insoluble.The impurities were separated, and the organic phase was washed with water until neutral. After drying over anhydrous sodium sulfate, the residue was purified by silica gel column to obtain 104.5 g of intermediate 1 in a yield of 89.3percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28342-75-8, its application will become more common.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Dandan; Tian Mi; He Haixiao; Li Jiangnan; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; (33 pag.)CN109535131; (2019); A;,
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21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 21524-34-5

General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol).

Statistics shows that 21524-34-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1,3,5-triisopropylbenzene.

Reference:
Article; Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime; Synlett; vol. 28; 18; (2017); p. 2460 – 2464;,
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58971-11-2, Name is 3-Bromophenethylamine, 58971-11-2, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

A mixture of 4-iodobenzoic acid (10.0 g, 40.32 mmol) in thionyl chloride (40 mL, 40.32 mmol) was stirred at 80 C for 16 hours. The reaction mixture was concentrated to give4-iodobenzoyl chloride (10.7 g, 99%) as a white solid. To a solution of 2-(3-bromophenyl)ethylamine (6.0 g, 29.99 mmol) and triethylamine (20 mL, 149.94 mmol) in dichioromethane (100 mL) at 0 C was added 4-iodobenzoyl chloride prepared above (9.6 g, 35.99 mmol) portionwise. The resulting mixture was stirred at 25 C for 4 hours and was then diluted with DCM (500 mL). Water (100 mL) was added to the reaction mixture and twolayers were separated. The organic layer was dried over anhydrous sodium sulfate, and was concentrated to give the title compound as a white solid (12 g, 93%). ?H NMR (400 MHz, CDC13) oe 7.75 (d, J= 8.4 Hz, 2H), 7.42 – 7.36 (m, 3H), 7.22 – 7.09 (m, 2H), 6.15 (s, 1H), 3.69- 3.64 (m, 2H), 2.91 – 2.87 (m, 2H).

Statistics shows that 3-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 58971-11-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LABADIE, Sharada; LIANG, Jun; ORTWINE, Daniel Fred; WANG, Xiaojing; ZHANG, Birong; ZBIEG, Jason; VINOGRADOVA, Maia; WANG, Tao; (150 pag.)WO2017/174757; (2017); A1;,
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55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-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.

Reference Production Example 8 (0631) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanato-2-methylbenzene (referred to as 8A). (0632) 1H-NMR (CDCl3) delta(ppm): 2.42 (3H, s), 7.00 (1H, dt, J=0.5, 8.0 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.39 (1H, dd, 1.5, 7.7 Hz).

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 55289-36-6.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SHIODA, Takayuki; ARIMORI, Sadayuki; (149 pag.)US2016/159755; (2016); 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 586-61-8 as follows. 586-61-8

To fuming nitric acid (5 mL) cooled to 5 was added neat 4-bromoisopropylbenzene(1.0 g, 5.023 mmol) dropwise at such a rate that the reaction temperature remained below 10. The reaction was stirred for 2 hours at 5-10, quenched with ice (50 g), extracted with ethyl acetate (50 mL), and the organic extract was washed with water (2×25 mL) and brine (25 mL), then dried over magnesium sulfate. filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash chromatography eluting with 5:95 ethyl acetate/hexanes to afford the title compound as a light yellow solid (1.03 g, 4.22 mmol, 84%). 1H NMR (300 MHz, CHLOROFORM-D) delta ppml.27 (d, J=6.99 Hz, 6 H) 2.75 – 3.23 (m, 1 H) 7.29 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=8.09 Hz, 1 H) 7.69 (d, J=2.21 Hz, 1 H); MS (DCI) m/z 261/263 (M+NH4)+.

According to the analysis of related databases, 586-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
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The chemical industry reduces the impact on the environment during synthesis 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life. 445-02-3

EXAMPLE 21 (E)-4-Cyclopentyl-2-[4-(5-methyl-tetrazol-1-yl)-3-trifluoromethyl-phenyl]-but-2-enoic acid thiazol-2-ylamide A solution of 2-(trifluoromethyl)-4-bromoaniline (4.8 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0 C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred at 0 C. for 10 min and then allowed to warm to 25 C. The reaction mixture was stirred at 25 C. for 2 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The crude residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtrated and washed with hexanes to afford N-(4-bromo-2-trifluoromethyl-phenyl)-acetamide (5.07 g, 90%) as an amorphous white solid: EI-HRMS m/e calcd for C9H7BrF3NO (M+) 281.8352, found 281.8348.

The chemical industry reduces the impact on the environment during synthesis 445-02-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sidduri, Achyutharao; US2002/35266; (2002); A1;,
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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.

Under an argon atmosphere, to a solution of 1,4-dibromo-2,5-difluorobenzene (10, 70.00 g) in diethyl ether (500 mL) was added dropwise 1.58 M n-butyl lithium solution in hexane (171 mL) at -78 C, and the mixture was stirred at same temperature for 2 min. The mixture was added quickly to the mixture of dry ice (about 300 g) and diethyl ether (600 mL), and the mixture was warmed up to room temperature. The precipitate was collected by filtration, and washed with diethyl ether. The obtained solid was treated with water (100 mL) and 1 M hydrochloric acid (500 mL), and extracted with diethyl ether. The organic layer was washed with brine and dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was washed with hexane, dried in vacuo to obtain 11a (53.29 g, 83%) as a pale yellow solid: 1H NMR (DMSO-d6) delta 7.78 (1H, dd, J = 6.4, 8.3 Hz), 7.89 (1H, dd, J = 5.9, 9.8 Hz); FAB-MS m/z 235, 237 [(M-H)-].

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 327-51-5.

Reference:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Misawa-Mukai, Hana; Hamaguchi, Wataru; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5235 – 5246;,
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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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows., 937046-98-5

Intermediate 7 A 3-(4-Aminopyrrolo [2, 1 -fj [ 1 ,2,4]triazin-7-yl)prop-2-yn- 1 -ol The starting material 7-bromopyrrolo[2, 1 -fj [ 1 ,2,4]triazin-4-amine was synthesized according to the procedure described in WO 2007/056170-A2 (Intermediate B). 7-Bromopyrrolo[2, 1 -fj [ 1 ,2,4]triazin-4-amine (1.0 g, 4.69 mmol), copper(I) iodide (89 mg, 0.47 mmol, 0.1 eq.) and tetrakis(triphenylphosphine)palladium(0) (542 mg, 0.47 mmol, 0.1 eq.) were charged into a microwave reactor vial and evacuated for 1 h. The vessel was then vented with argon, pyrrolidine (15 mL) and 2-propyn-l-ol (2.63 g, 47 mmol, 10 eq.) were added, and the vessel was crimp-capped and heated to 85C for 120 min in a single-mode microwave device. After cooling, the reaction mixture was poured into 120 mL of concentrated aqueous ammonium chloride solution which was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and evaporated, and the residue was purified by flash chromatography (Biotage silica column, ethyl acetate). The resulting product (222 mg) appeared pure by LC-MS (method 6) and was used for further transformations. HPLC (method 2): ? = 2.59 min; LC-MS (method 6): Rt = 0.28 min; MS (ESIpos): m/z (%) = 189.2 (100) [M+Hf.

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Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Bayer Pharma Aktiengesellschaft; KLAR, Juergen; VOEHRINGER, Verena; TELSER, Joachim; LOBELL, Mario; SUessMEIER, Frank; LI, Volkhart Min-Jian; BOeTTGER, Michael; GOLZ, Stefan; LANG, Dieter; SCHLEMMER, Karl-Heinz; SCHLANGE, Thomas; SCHALL, Andreas; FU, Wenlang; WO2013/4551; (2013); A1;,
Bromide – Wikipedia,
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955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 955959-84-9

General procedure: 26.8 g (100 mmol) of 8H-quino[4,3,2-kl]acridine [111180-95-5], 35.6 g (100 mmol), 5?-iodo-1,1:3?,1?-terphenyl [87666-86-2], 27.6 mg / g (200 mmol) of potassium carbonate, 28.4 g g (200 mmol) of sodium sulfate, copper powder of 1.3gg (20mmol), Glass Beads (Diameter: 3 mm) And a mixture of 300 ml of nitrobenzene is heated under reflux while stirring well for 16 hours under reflux. After cooling down, Add 1000 ml of methanol, Suction and filter the solid, Wash 3 times with 300 ml of methanol each time. This solid is extracted from 1000 ml of water by stirring with high temperature. After suction filtration, Wash every 2 times with 200 ml of hot water each time. After washing 3 times with 200 ml of methanol each time, Dry under reduced pressure. The resulting crude product is o-xylene (initial dose: 250 ml) 5 times a high temperature extract, Next, 2 times fractional sublimation (p is about 10-5 mbar, T about 310 C). Yield: 28.3 mug g (57 mmol), 57%; Purity: 99.99% by HPLC.

Statistics shows that 955959-84-9 is playing an increasingly important role. we look forward to future research findings about 4-(4-Bromophenyl)dibenzo[b,d]furan.

Reference:
Patent; Merck Patent GMBH; Syu Toe-ssel-pil-rip; Pa Reu-ham-a-mi-reu; Yo Syu-ten-do-mi-ni-keu; Ru De-mang-o-rel-ri; Geu Ro-sseu-man-to-bi-a-seu; Keu Roe-beo-yo-na-seu; (57 pag.)KR2019/86028; (2019); A;,
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