Category: bromides-buliding-blocks

583-75-5, These common heterocyclic compound, 583-75-5, name is 4-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.

3,6-Dibromotoluene In a 2000 ml beaker containing 400 ml of 23percent aqueous HBr, 46.5 g (0.25 mol) of melted 2-methyl-4-bromoaniline was slowly added. This mixture was stirred for 20 minutes using a mechanical stirrer, then cooled to -5¡ã C. Then a solution of 22.4 g (0.33 mol) of NaNO2 in 130 ml of water was added dropwise over 1 hour at this temperature. The diazonium reagent obtained was added in several portions to a solution of 35.9 g (0.25 mmol) of CuBr in 100 ml of 47percent HBr at 0¡ã C. The resulting mixture was warmed to 70¡ã C., stirred for 30 minutes at this temperature, and, then, cooled to room temperature. The product was extracted with 3*200 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Firstly, the crude product was purified using short column with Silica Gel 60 (40-63 mum, d 60 mm, 140 mm; eluant: hexanes). Fractional distillation gave colorless oil, b.p. 100-102¡ã C./10 mm Hg. Yield, 36.1 g (58percent). Anal. calc. for C7H6Br2: C, 33.64; H, 2.42. Found: C, 33.79; H, 2.50. 1H NMR (300 MHz, CDCl3): delta 7.39 (m, 1H, 5-H), 7.37 (m, 1H, 3-H), 7.18 (m, 1H, 6-H), 2.38 (s, 3H, Me). 13C NMR (75 MHz, CDCl3): delta 139.9, 133.6, 133.5, 130.3, 123.5, 120.9, 22.7.

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 583-75-5.

Reference:
Patent; Voskoboynikov, Alexander Z.; Izmer, Vyatcheslav V.; Asachenko, Andrey F.; Nikulin, Mikhail V.; Ryabov, Alexey N.; Lebedev, Artyom Y.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135597; (2007); A1;,
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Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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. 57946-63-1

2-Bromo-4-(trifluoromethyl)aniline (3. 5g, 14.58 mmol), 1H-pyrazole (1 .98g, 29.2 mmol), N1,N2-dimethylethane-1,2-diamine (0.78 ml, 7.29 mmol), cesium carbonate (10.45g, 32.1 mmol) was added to degassed 1,4-dioxane (15 ml) in a sealed tube and copper(i) iodide (0.55g, 2.92 mmol) was added. The tube was sealed and heated at 120 ¡ãC for 72h. After the solution was cooled, the mixture was passed through a pad of celite and the filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed withbrine, dried over Na2SO4 and concentrated. The crude was purified by column chromatography to obtain the product as off white solid (2.7g, 83percent). LCMS (ESI): mlz 228.39(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57946-63-1, its application will become more common.

Reference:
Patent; LUPIN LIMITED; RAMDAS, Vidya; LORIYA, Rajeshkumar, Maganlal; BANERJEE, Moloy; PATIL, Pradeep, Rangrao; JOSHI, Advait, Arun; DATRANGE, Laxmikant, Shamlal; WALKE, Deepak, Sahebrao; KHAN, Talha, Hussain; DAS, Amit, Kumar; GOTE, Ganesh, Navinchandra; KALHAPURE, Vaibhav, Madhukar; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (234 pag.)WO2017/37682; (2017); A1;,
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4766-33-0, These common heterocyclic compound, 4766-33-0, name is 5-Bromonaphthalen-1-amine, 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.

General procedure: The substituted 1-naphthylamine (10 mmol), 2-picolinic acid (12.5 mmol) and Et3N (20 mmol,2.8 mL) were dissolved in DCM (40 mL) followed by dropwise addition of POCl3 (1.88 mL) at 0C. The resulting mixture was stirred at 0C for 0.5 h and warmed to room temperature for 2 h. Then the reaction mixture was cooled to 0C. Ice water was added slowly to quench the reaction. The organic layer was collected, and the aqueous phase was extracted with DCM. The combined organic phase was washed by saturated NaHCO3 and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was recrystallized from i-propyl alcohol to give desired product.

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 4766-33-0.

Reference:
Article; Guan, Dinghui; Han, Lu; Wang, Lulu; Song, He; Chu, Wenyi; Sun, Zhizhong; Chemistry Letters; vol. 44; 6; (2015); p. 743 – 745;,
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Some common heterocyclic compound, 615-59-8, name is 1,4-Dibromo-2-methylbenzene, molecular formula is C7H6Br2, 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. 615-59-8

(1) 2,5-dibromotoluene (10 mmol, 2.5 g), 4-methoxycarbonylbenzeneboronic acid (24 mmol, 4.33 g) under N2 protection.caesium fluoride (40 mmol, 6.0 g) was placed in a 250 mL three-necked flask, and 5% (1.2 to 2.0 g) of Pd (PPh3) catalyst was added.100 mL of anhydrous THF was used as a solvent, and refluxed at 67 C.After completion of the reaction, the product was isolated by silica gel column chromatography (petroleum ether, dichloromethane) to give a pink solid 2.91 g, yield 81%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 615-59-8, its application will become more common.

Reference:
Patent; Shandong Normal University; Dong Yubin; Wang Jiancheng; Liu Congxue; Hu Yuhong; (14 pag.)CN108640906; (2018); A;,
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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. 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2635-13-4

Benzo[1,3]dioxole-5-carbaldehyde (1.80 g, 11.96 mmol), 5-bromobenzo[1,3]dioxole (2.65 g, 13.16 mmol), and n-butyl lithium (5.26 ml, 13.16 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (5% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give bis-benzo[1,3]dioxol-5-yl-methanol as a light brown oil (2.69 g, 83%): 1H-NMR (CDCl3) 6.86-6.74 (m, 6H, Ar), 5.93 (s, 4H, 2CH2), 5.68 (d, J=3 Hz, 1H, CHOH), 2.16 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1083181-43-4, name is 6-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole, 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 1083181-43-4, 1083181-43-4

The title compound is prepared according to General Procedure 8 described for Intermediate 14, using 6-bromo-1-methyl-1 H-1 ,2,3-benzotriazole (Intermediate 80, 45 mg; 0.21 mmol; 1 eq.), bis(pinacolato)diboron (108 mg; 0.42 mmol; 2 eq.), potassium acetate (125 mg; 1.27 mmol; 6 eq.), Pd(dppf)CI2 (27 mg; 0.03 mmol; 0.15 eq.) in DMSO (2 mL). Conditions: 90 C overnight. The crude 1-methyl-6-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 – – 1 ,2,3-benzotriazole (80 mg; 0.10 mmol; 45%; brown solid; UPLC purity: 85%) is used in the next step without further purification.

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, 6-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole, 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;,
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16518-62-0, These common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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.

General procedure: A mixture of N,N-dimethylaniline 1 (2.0 mmol), indole 2 (1.0mmol), K2S2O8 (1.5 equiv), and CH3CN (3 mL) was taken in aflask and stirred at r.t. for 2?4 h (Scheme 2). After completion ofthe reaction (monitored by TLC), water (5 mL) was added andthe mixture was extracted with ethyl acetate (3 ¡Á 5 mL). Thecombined organic phase was dried over anhydrous Na2SO4, filtered,and evaporated under reduced pressure. The resultingcrude product was purified by silica gel chromatography using amixture of hexane/ethyl acetate (4:1) as eluent to afford an analyticallypure sample of product 3.

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 16518-62-0.

Reference:
Article; Singh, Manjula; Yadav, Arvind K.; Yadav, Lal Dhar S.; Singh, Rana Krishna Pal; Synlett; vol. 29; 17; (2018); p. 2306 – 2310;,
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Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. 65896-11-9

General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Article; Shi, Yajie; Zhou, Qifan; Du, Fangyu; Fu, Yang; Du, Yang; Fang, Ting; Chen, Guoliang; Tetrahedron Letters; vol. 60; 40; (2019);,
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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. 1252934-30-7, name is 3-(Bromomethyl)-1,1-difluorocyclobutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1252934-30-7

Ethyl (R)-12-hydroxy-l l-methoxy-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l- a]pyrrolo[l,2-c]phthalazine-7-carboxylate (59 mg, 150 muetaiotaomicron) was combined with 3- (bromomethyl)-l,l-difluorocyclobutane (85 mg, 460 mumol) and Potassium Carbonate (85 mg, 0.61 mmol) in DMF (0.4 mL). The mixture was stirred at 70 C for 55 minutes, and then cooled to room temperature. Aqueous 1M lithium hydroxide (334 mu) was added and the mixture was stirred at 35 C for 30 minutes. The mixture was cooled to room temperature, diluted with TFA, and purified by preparative HPLC to provide (R)-12-((3,3-difluorocyclobutyl)methoxy)-l l- methoxy-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7- carboxylic acid as a TFA salt. l NMR (400 MHz, Acetonitrile-d3) delta 8.45 (s, IH), 7.39 (s, IH), 7.26 (s, IH), 6.95 (d, J = 0.9 Hz, IH), 4.84 (d, J = 6.2 Hz, IH), 4.16 (qt, J = 12.8, 6.5 Hz, 2H), 3.92 (s, 3H), 2.85 – 2.33 (m, 7H), 1.89 (ddd, J = 12.6, 7.8, 2.7 Hz, IH), 1.62 (ddd, J = 12.4, 10.8, 7.8 Hz, IH), 1.36 (s, 3H), 0.66 (s, 3H). 19F NMR (376 MHz, Acetonitrile-d3) delta -77.33 , -84.17 – -85.00 (m), -93.89 – -94.83 (m). MS (m/z) 461.3 [M+H]+.

The synthetic route of 1252934-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); A1;,
Bromide – Wikipedia,
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72678-19-4, 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. 72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below.

A mixture of 2,6-dibromo-4-(trifluoromethyl)aniline [72678-19-4] (5.13 g, 16.1 mmol), triemthylboroxine [823-96-1] (5 mL, 35.3 mmol), Pd(PPh3)4 (1.11 g, 1.00 mmol) and K2C03 (sat., aq., 74 mL) in DME (74 mL) was stirred at 150 C for 2 h. The mixture was concentrated in vacuo and the residue was taken up in water and DCM. The organic phase was separated, dried (MgS04), filtered and evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 50:50) to afford 1-131 (1.86 mg, 61%) as a brown oil.

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; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
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