Month: August 2021

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 50548-45-3 as follows. Application In Synthesis of 1-Bromodibenzo[b,d]furan

180 g (728 mmol) of 1-bromodibenzofuran are dissolved in 1500 ml of dry THF and cooled to -78°C. 305 ml (764 mmol I 2.5 M in hexane) of n-butyllithium are added over the course of about 5 mm. at this temperature, and the mixture is subsequently stirred at -78°C for a further 2.5 h. 151 g (1456 mmol) of trimethyl borate are added as rapidly as possible at this temperature, and the reaction is slowly allowed to come to room temperature(about 18 h). The reaction solution is washed with water, and the solid which has precipitated out and the organic phase are dried azeotropically with toluene. The crude product is washed by stirring with toluene/methylene chloride at about 40°C and filtered off with suction. Yield: 146 g (690 mmol),95percent of theory.

According to the analysis of related databases, 50548-45-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; PARHAM, Amir Hossain; JATSCH, Anja; EBERLE, Thomas; GROSSMANN, Tobias; KROEBER, Jonas Valentin; DOBELMANN-MARA, Lars; (100 pag.)WO2016/198144; (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. 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 268733-18-2

General procedure: 4-Bromo-3,5-bis-(trifluoromethyl)aniline (616 mg, 2 mmol, 1 equiv), potassium carbonate (829 mg, 6 mmol, 3 equiv), Pd(PPh3)4 (231 mg, 0.2 mmol, 0.1 equiv), DMF (5 mL, 0.4 M) and (MeO)3B (0.28 mL, 2 mmol, 1 equiv) were added to a flask and the contents heated to 110 C overnight. The reaction solution was filtered using silica gel, Celite, and sea sand. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (1:5 EtOAc:Hex), to give 4-methyl-3,5-bis(trifluoromethyl)aniline (760 mg, 67%). 1H NMR (300 MHz, DMSO-d6): delta 2.42 (s, 3H), 3.88 (s, 2H), 7.09 (s, 2H). This aniline was used for general procedure A (EtOAc:Hex 1:20 ? 1:10) (630 mg, 51%). Slightly brown solid. Mp 192-193 C. 1H NMR (300 MHz, DMSO-d6): delta 2.49 (s, 3H), 7.02 (d, J = 8.8 Hz, 1H), 7.47 (dd, J1 = 8.8 Hz, J2 = 2.7 Hz, 1H), 7.87 (d, J = 2.6, 1H), 8.41 (s, 2H), 10.75 (s, 1H), 11.48 (s, br, 1H). HRMS (APCI), m/z calcd for C16H10ClF6NO2-H: 396.0226, found 396.0238.

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:
Article; Lee, Ill-Young; Gruber, Todd D.; Samuels, Amanda; Yun, Minhan; Nam, Bora; Kang, Minseo; Crowley, Kathryn; Winterroth, Benjamin; Boshoff, Helena I.; Barry III, Clifton E.; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 114 – 126;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 73918-56-6, These common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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: To a solution of compound 31 (99 mg, 0.30 mmol) in anhydrous DMF (5.0 mL) were added EDC (75 mg, 0.39 mmol) and HOBt (45 mg, 0.33 mmol) and then stirred under ice water bath for 5 min, then the selected amine (0.36 mmol) were employed to the reaction mixture for another 15 min at 0 C and stirred at room temperature for 3 h. The mixture was extracted with ethyl acetate, washed with water and brine, and then dried over anhydrous Na2SO4. The crude product was purified by column chromatography (SiO2, petroether/ethyl acetate) to afford target compounds 32-44.

Statistics shows that 2-(4-Bromophenyl)ethanamine is playing an increasingly important role. we look forward to future research findings about 73918-56-6.

Reference:
Article; Wu, Jing; Yu, Linxi; Yang, Feifei; Li, Jingjie; Wang, Peng; Zhou, Wenbo; Qin, Liwen; Li, Yunqi; Luo, Jian; Yi, Zhengfang; Liu, Mingyao; Chen, Yihua; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 340 – 351;,
Bromide – Wikipedia,
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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. 4263-52-9, name is Sodium 2-bromoethanesulphonate, This compound has unique chemical properties. The synthetic route is as follows., name: Sodium 2-bromoethanesulphonate

Phosphorus pentachloride (commercially available, for example, from Aldrich) (1 1.8 g, 57 mmol) was added portionwise to stirred sodium bromoethanesulfonate (commercially available, for example, from Aldrich) (4.0 g, 19 mmol) over five minutes. When the addition was complete, the suspension was heated to 1 10 0C for 2 h before cooling to 21 0C and then pouring onto ice. The product was extracted with dichloromethane and the organic layer was washed successively with water, sodium bicarbonate and water. The organic solution was dried over magnesium sulfate and evaporated to give the title compound (3.24 g), 1H NMR delta (CDCI3) 4.12 (2H, t, J = 8 Hz), 3.79 (2H, t, J = 8 Hz).

According to the analysis of related databases, 4263-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/47336; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 348-57-2, A common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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 1-bromo-2,4-difluorobenzene (1.65 g, 8.57 mmol) in diethyl ether (Et2O; 10 mL) were added sequentially n-butyllithium (n-BuLi, 2.3 Molar (M) in hexane; 3.70 mL, 8.57 mmol) at -70° C. and the above ester (2.40 g, 8.57 mmol) in Et2O (5 mL) after 15 minutes (min). The reaction mixture was stirred for 1 h at -70° C., warmed to RT and stirred for another 2 h. The reaction mixture was quenched with aq NH4Cl solution and extracted with EtOAc (3.x.20 mL). The combined organic layers were washed with H2O, washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude compound was purified by column chromatography (eluting with EtOAc/hexane) to afford ketone B (1.30 g, 3.73 mmol, 43percent) as a yellow liquid. 1H NMR (500 MHz, CDCl3): 88.62 (s, 1H), 8.08-8.04 (m, 2H), 7.74-7.70 (m, 1H), 7.05-6.95 (m, 1H), 6.88-6.78 (m, 1H). MS (ESI): m/z 347, 349 [(M++1)+2].

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.; US2012/329788; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 25121-87-3, 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 25121-87-3 as follows.

Take a 500 ml three-neck round bottom bottle and place the stirrer with the upper addition funnel.After drying, it is filled with nitrogen;First, 92 mL of lithium diisopropylamide (0.184 mol, 2.3 eq) was added at a concentration of 2M, followed by dissolving 23.841 g of compound P01 (0.08 mol, 1 eq) in 150 mL of anhydrous tetrahydrofuran in an addition funnel.And the resulting solution was added dropwise to a three-necked round bottom bottle at -78 C.After the reaction gradually returns to temperature, the reaction is continued for 18 hours;The reaction was stopped with 120 mL of saturated aqueous sodium bicarbonate solution.It was then extracted with 200 mL of ethyl acetate and repeated 3 times.The obtained extract is sequentially added with magnesium sulfate to dry, filtered and spin-dried;The crude product was purified by recrystallization from ethanol to give 22.172 g of 3,6-dibromothieno[3,2-b]thiophene (yield: 93%).

According to the analysis of related databases, 25121-87-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Jizhichuang New Materials Institute Co., Ltd.; Wei Dingwei; Xie Kunshan; Ding Huanda; Chen Zhikuan; (39 pag.)CN109836436; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 31543-75-6, 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. 31543-75-6, name is 2,4-Dibromo-1-methylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,4-Dibromotoluene (1.000 g, 4.00 mmol) and freshly purifiedNBS (0.925 g, 5.20 mmol) were solubilized in 12 mL of 1,2-dichloroethane under inert atmosphere. The solution wasrefluxed during 10 min and azobisisobuthyronitrile AIBN, 0.328 g,2.00 mmol) was added. The resulting suspension was stirred andrefluxed during 6 h. The reaction was monitored by TLC cyclohexane100%. Then, the reaction mixture was evaporated and asolution of cold cyclohexane/dichloromethane 1:1 was added toprecipitate side products (white solid). After the filtration andevaporation, the crude product (1.476 g, 4.49 mmol) was directlyused without purification.

The synthetic route of 2,4-Dibromo-1-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roussel, Emile; Tran-Nguyen, Viet-Khoa; Bouhedjar, Khalid; Dems, Mohamed Abdesselem; Belaidi, Amine; Matougui, Brahim; Peres, Basile; Azioune, Ammar; Renaudet, Olivier; Falson, Pierre; Boumendjel, Ahcene; European Journal of Medicinal Chemistry; vol. 184; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-46-1, 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. 766-46-1, name is 2′-Bromophenylacetylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 25 mL of flask, t-BuLi (2 mmol, 1.6 M in pentane) was added dropwise at -78 C to a stirred solution of o-bromoethynylbenzene (1 mmol, 181 mg) or its derivative (1 mmol) in Et2O (5 mL) and the reaction mixture was allowed to warm to room temperature. After stirring at room temperature for 1 h, S8 (0.25 mmol, 64 mg) was added and the reaction was stirred at room temperature for 2 h. The solvent of the reaction mixture was evaporated under vacuum and THF (5 ml) was added. After that, an electrophile (2 mmol) was added dropwise at room temperature. After stirring at room temperature for 1 h, the solvent of the reaction mixture was evaporated under vacuum. The residue was purified by chromatography to give products 4 and 6.

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

Reference:
Article; Wang, Zitao; Geng, Weizhi; Wang, Hanliu; Zhang, Shaoguang; Zhang, Wen-Xiong; Xi, Zhenfeng; Tetrahedron Letters; vol. 52; 51; (2011); p. 6997 – 6999;,
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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Safety of 4,5-Dibromobenzene-1,2-diamine

General procedure: To a 10 mL vial were added o-diaminobenzene 2 (0.2 mmol, 1.0 equiv), DIPEA(0.24 mmol, 1.2 equiv), and toluene (2 mL), followed by the slow addition of a solution of-acetoxy allenoate 1 (0.24 mmol,1.2 equiv) in toluene (2 mL). The solution was stirred for 12 h atroom temperature. The reaction mixture was concentrated under reduced pressure, and the residuewas purified by silica gel column chromatography using petroleum ether and ethyl acetate (30:1 to15:1 v/v) as the eluent to give the corresponding annulations product 3.

The synthetic route of 49764-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yi-Fan; He, Cheng-Yu; Hou, Longlei; Tian, Ping; Lin, Guo-Qiang; Tong, Xiaofeng; Synlett; vol. 29; 9; (2018); p. 1176 – 1180;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 103-64-0, name is (2-Bromovinyl)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 103-64-0, Quality Control of (2-Bromovinyl)benzene

beta-Bromostyrene (7 mL, 54.57 mmol) was dissolved in 64 mL Et2O and cooled to -78 C. t-BuLi (1.6M in pentane, 64 mL, 102.4 mmol) was added over 40 min. The mixture was stirred at -78 C for 1 h, at which time (R)-7-allyl-3-isobutoxy-7-methylcyclohept-2-enone (4, 7.8335 g, 33.14 mmol) in 15 mL Et2O was added by cannula with a 5 mL rinse. After 90 min, the reaction was warmed with an ice bath and stirred for 1 h. The reaction was quenched with 10% HCl (100 mL), and the volatiles removed in vacuo. To the residue was added 100mL THF. The mixture was then heated to 50 C for 12 h. After cooling to room temperature, the mixture was extracted 4 * 100mL Et2O. The combined organic extracts were dried over MgSO4, and evaporated in vacuo. Silica gel chromatography (5 * 17 cm, ~700 mL 20:1 hexanes:EtOAc then~1.6 L 15:1 hexanes:EtOAc) afforded the title compound as a viscous yellow oil (8.0542 g, 91% yield). RF = 0.23 (10:1 Hexane:EtOAc); 1H NMR (300 MHz, CDCl3) delta 7.45-7.27 (m, 5H), 6.90 (s, 2H), 6.31 (s, 1H), 5.68 (dddd, J = 6.6, 8.1, 10.5, 17.1 Hz, 1H), 5.09-5.01 (m, 2H), 2.66-2.61 (m, 2H), 2.47 (dd, J = 6.6, 14.1 Hz, 1H), 2.14 (dd, J 8.1,14.1 Hz, 1H), 1.93-1.80 (m, 3H), 1.70-1.60 (m, 1H), 1.27 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 204.5, 158.3, 136.5, 133.7, 133.1, 129.0, 128.7, 128.3, 126.9, 126.9, 118.3, 46.0, 44.3, 44.2, 38.5, 26.6, 17.4; IR (Neat Film NaCl) 3075, 3026, 2925, 1640, 1582, 1450, 1344, 1250,1217, 963, 916, 752, 694 cm-1; HRMS m/z calc’d for C19H22O [M]+: 266.1671, found 266.1668; [alpha]D24.8 +33.70 (c 1.19, CHCl3, 88% ee).

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

Reference:
Article; Harned, Andrew M.; Stoltz, Brian M.; Tetrahedron; vol. 75; 24; (2019); p. 3166 – 3177;,
Bromide – Wikipedia,
bromide – Wiktionary