Month: December 2020

Synthetic Route of 39478-78-9,Some common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 0.003 mol) and 4-chlorophenylboronic acid (20.2 g, 0.13mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2- dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 200C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is heated at reflux for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino-4′-chloro-4-methylbiphenyl (21.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2009/150093; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 64695-79-0, name is 2-Bromo-4,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H4BrF2N

To a solution of 2-bromo-4,5- difluoroaniline (1.2 g, 4.3 mmol) in DMF (4 mL) was added tetrakis(triphenylphosphine)palladium(0) (400 mg, 0.34 mmol) and zinc cyanide (800 mg, 6.8 mmol). The solution was sparged with nitrogen and heated at 120 C for 30 minutes in a Biotage microwave reactor. The resulting suspension was filtered and concentrated in vacuo to afford the crude product. Purification by column chromatography (CI 8 reverse phase, water + 0.1% NH3 H20 -> MeCN + 0.1% NH3 H2O) afforded the desired 2-Amino-4,5-difluorobenzonitrile.

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 64695-79-0.

Reference:
Patent; INCEPTION 1, INC.; JACINTHO, Jason, Duarte; CLARK, Ryan, Christopher; SHENG, Tao; OBALLA, Renata, Marcella; STOCK, Nicholas, Simon; ROPPE, Jeffrey, Roger; (161 pag.)WO2017/192304; (2017); 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. 6911-87-1, name is 4-Bromo-N-methylaniline, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Weigh BTC (58mg, 0.2mmol) in a 25mL two-neck bottle.Add 5 mL of anhydrous dichloromethane, magnetically stir, add equivalents of N-methyl-p-bromoaniline, triethylamine (0.25 mmol) and 5 mL of dichloromethane to a 25 mL constant pressure dropping funnel.Under ice bath, slowly add dropwise. After the addition, the ice salt bath was removed and stirred at room temperature for 4 h.HZA (40 mg, 0.1 mmol) was added to a 10 ml vial, and traces of DMAP, 5 mL of dichloromethane were added, and magnetically stirred at room temperature until completely dissolved.The solution was slowly added dropwise to the reaction liquid in the above step under an ice salt bath.At the end of the addition, the ice salt bath was removed and stirred at room temperature. After the reaction is completed, 3 to 6 times the volume of the reaction liquid is added to the above reaction liquid, and the mixture is extracted with ethyl acetate for 3-5 times. The organic layer is combined, washed with a saturated NaCI solution, dried over anhydrous Na2SO?Concentrate the crude product as a yellow oil, then the crude product was taken from petroleum ether:Ethyl acetate with a volume ratio of 20:1 mixed solvent elution, thin layer detection,Collecting an eluent that is strongly UV at 254 nm and less polar than HZA,The combined eluate and the product obtained by evaporating the solvent under reduced pressure are dried to obtain HZAM-17.The yield was 93%.

The synthetic route of 6911-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Zhan Zhajun; Shan Weiguang; Chen Yan; Shu Renhuan; Wang Jianwei; Ma Liefeng; (31 pag.)CN109956952; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2,2-dimethylpropane

To a solution of 0,8g(33,10 mmol)of magnesium turnings and 2,0g(13,2 mmol)of 1- bromo-2,2-dimethylpropane in 10 mL diethyl ether was added a solution of 1.42 g (7.76 mmol) of 4-bromostyrene and 69 mg (0.13 [MMOL) OF NI] (dppf) [C12.] The resulting reaction mixture was heated at refluc for 8 h. The reaction was quenched with [50%] saturated NH4Cl, and was extracted with MTBE (2 x 150 mL). The combined extractions were washed with water, dried and concentrated. Flash chromatography on a Biotage 40M cartridge with hexanes as the eluant afforded 1.74 g of the title compound [: LH NMR (500 MHZ) a 0.] 93 (s, 9H), 2.49 (s, 2H), 5.20 (d, J = 10.9, 1H), 5.73 (d, [J] = 17.6, 1H), 6.72 (dd, [JL] [= 17.] 6, J2 [= 10.] 8,1H), 7.10 (d, J = 8.2, 2H), 7.33 (d, J = 8.0, 2H); ESI-MS 161 (M+H); LC-1: 4.4 min.

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/35538; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 3638-73-1, 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. 3638-73-1, name is 2,5-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3. Synthesis of 2,5-dibromophenol; Sodium nitrite (65.2 mmol) was added in several portions to a solution of 2,5-dibromobenzenamine (55.8 mmol) in trifluoroacetic acid (80 mL) at 0 C. The resulting solution was added to a boiling solution of sodium sulfate (10 g) in 50% sulfuric acid (120 mL) and the reaction mixture was maintained at reflux for 1 h. Then the product was steam-distilled and the distillate was extracted with dichloromethane (2¡Á200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to provide 2,5-dibromophenol in 41% yield as a yellow solid.

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, 2,5-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/16297; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4263-52-9, name is Sodium 2-bromoethanesulphonate, 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 4263-52-9, Safety of Sodium 2-bromoethanesulphonate

EXAMPLE 2 Production of Disodium 2,2′-dithiobis Ethane Sulfonate To a mixture of 50.1 g of water with 24.4 g of thioacetic acid, 50.7 g of 25% aqueous sodium hydroxide solution were added dropwise at 10-30 C. This solution was added dropwise to a solution of 63.3 g of sodium 2-bromoethane sulfonate and 70 g of water at 50-70 C. and allowed to react at 80-90 C. for 2 hours. Thereto 54.2 g of 25% aqueous sodium hydroxide solution were added and allowed to react at refluxing temperature (about 105 C.) until the end of the reaction was confirmed by HPLC. After addition of 3.25 g of acetic acid, the reaction mixture was refluxed for 6 hours and then cooled to about 30 C. The pH of the mixture was adjusted to 7.3 with 25% sodium hydroxide solution. Oxygen was allowed to react with 260 mL of aqueous sodium 2-mercapto ethane sulfonate solution obtained above at about 30 C. and 0.5-0.6 MPa of oxygen pressure. When the end of the reaction was confirmed by HPLC, the reaction was stopped and the mixture was neutralized with acetic acid. The mixture was heated to about 70 C. and it was observed that the mixture had been dissolved. After that, the mixture was filtered with a filtering assistant agent (radiolite) and the filtering assistant agent was washed with 10 g of water. The mixture was concentrated under reduced pressure (about 10 kPa) at 70 C. When the amount of the distilled out water became 60 g, the concentration was stopped and it was observed that the mixture remained dissolved at about 75 C. Cooling the mixture, crystallization began at 60+-5 C. After aging for about 30 minutes, the mixture was cooled to 25 C. and the crystals were aged for 2 hours at 25 C. The crystals were filtered out and washed with 24 g of water being cooled to 2 C. and then 48 mL of 70% aqueous ethanol solution. Drying the crystals at about 70 C. afforded 39.1 g of substantially pure disodium 2,2′-dithiobis ethane sulfonate crystals. The yield was 77.6% after crystallization. The purity of the product was 99.4%. According to the present invention, compounds of Formula II, such as disodium 2,2′-dithiobis ethane sulfonate, can be produced by an efficient procedure from available, relatively less expensive raw compounds in good yield with high purity. The above details are not limitative of the invention, which is defined by the scope of the following claims. It will be appreciated by those skilled in the art that changes could be made to the embodiments described above without departing from the broad inventive concept thereof. It is understood, therefore, that this invention is not limited to the particular embodiments disclosed, but it is intended to cover modifications within the spirit and scope of the present invention as defined by the appended claims.

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; BioNumerik Pharmaceuticals, Inc.; US2005/137419; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

Intermediate XI6-Bromo-1,2-dimethyl-1H-benzoimidazole A solution of 4-bromo-2-methylamino-aniline (1.10 g) in acetic acid (15 mL) was stirred at 130 C. for 2 h. After cooling to ambient temperature, the solution was concentrated under reduced pressure and the residue was taken up in ethyl acetate. The resulting solution was washed with 10% aqueous K2CO3 solution and brine and dried (MgSO4). The solvent was removed and the remainder was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 99:1:0.1->9:1:0.1) to give the title compound as a solid.Yield: 0.58 g (47% of theory); Mass spectrum (ESI+): m/z=225/227 (Br) [M+H]+.

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/108578; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2789-89-1, These common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, 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 45 Preparation of 3,4-Bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide 3,4-Bis(4-bromophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide (47.2 mg, 57%) as a target product was obtained under the condition of 90 C. for 30 hours, by the same reaction as the Example 1 above, except for using diphenylphosphinic acid (32.7 mg, 0.15 mmol) instead of using phenylphosphonic monoethyl ester of the Example 1 above, and using 1,2-bis(4-bromophenyl)ethyne (75.6 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. 1H NMR (400 MHz, CDCl3) delta 7.94-7.89 (m, 2H), 7.66-7.51 (m, 6H), 7.47 (tt, J=7.7, 1.2 Hz, 1H), 7.39-7.34 (m, 1H), 7.28 (app d, J=8.7 Hz, 2H), 7.15 (d, J=8.2 Hz, 2H), 7.09 (app d, J=8.7 Hz, 2H), 7.01 (dd, J=8.0, 4.7 Hz, 1H).

The synthetic route of 2789-89-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; Lee, Phil Ho; Park, Young Chul; Jeon, In Cheol; Seo, Jung Min; Seo, Bo Ram; US2015/344506; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 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.

Under an Ar atmosphere, to a 500 ml, three-neck flask, Compound C (5.00 g) was put and dissolved in dehydrated THF (100 ml), and nBuLi (1.6 M in hexane, 12.6 ml) was added dropwise thereto at about -78 C. After stirring at about -78 C. for about 1 hour, a THF solution (100 ml) of B (7.01 g) was added dropwise thereto, followed by stirring for about 16 hours while gradually increasing the temperature to ambient temperature. Water was added to the resultant product, and an organic layer was extracted with CH2Cl2, separated, and dried with MgSO4. Solvents were removed by distillation under a reduced pressure. The crude product thus obtained was dissolved in toluene (100 ml), and pTsOH (11.5 g) was added thereto, followed by heating and stirring at about 80 C. for about 6 hours. After the reaction, a precipitate thus produced was obtained by filtering and separated by recrystallization to obtain 6.24 g (yield 62%) of Intermediate D. The molecular weight of Intermediate D measured by FAB-MS was 499.

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; SAMSUNG DISPLAY CO., LTD.; SAKAMOTO, Naoya; AKASHI, Nobutaka; (46 pag.)US2020/20866; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. Quality Control of 1-Bromo-2,4,5-trifluorobenzene

In an oven-dried flask, dried halogen-group-containing compounds (2.3 equiv) were added to dry THF containing magnesium metal (Mg) (2.3 equiv, with glass pieces to activate the magnesium metal) at room temperature under nitrogen. The reaction mixture was stirred vigorously until Grignard generation occurred. The lactone (1 equiv dissolved in 40 mL of THF) was added dropwise to the Grignard reagent solution, and the mixture was stirred at room temperature for 16 h and monitored by TLC. The mixture was treated with saturated aqueous NH4Cl (20 mL) and then extracted with AcOEt (3¡Á10mL). The combined organic phases were dried over Na2SO4 and the solvent was removed by an evaporator. The residue was purified by silica-gel column chromatography (AcOEt/hexane). In another experiment, the ring-opening reactions of homoserine lactone with select Grignard reagents were carried out using 2.7 equiv ArMgBr at r.t. and 50C for 2 h.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guendo?du, Oezlem; Turhan, P?nar; Koese, Aytekin; Altunda?, Ramazan; Kara, Yunus; Tetrahedron Asymmetry; vol. 28; 9; (2017); p. 1163 – 1168;,
Bromide – Wikipedia,
bromide – Wiktionary