Tag: M.W=200-300

Application of 18599-22-9, 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 18599-22-9 as follows.

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil.

According to the analysis of related databases, 18599-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 24358-62-1, 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. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding ketone (20 mmol, 1.0 eq) and CH3OH (20 mL) were added to a 250 mL Schlenk tube containing [RhCp*Cl2]2 (61.8 mg, 100 mumol, 0.005 equiv) and HCOONH4 (6.36 g, 100 mmol, 5.0eq). The brown mixture was frozen, and the whole system was evacuated. The system was closed and then stirred at 70 C for 7 h. After the dark green resulting solution was cooled to room temperature, 1M aqueous HCl solution (38.4 mL) was added, and the mixture was washed twice with CH2Cl2 (5 mL) to remove the neutral compounds. After addition of a cold 12 M aqueous NaOH solution (3.6 mL) to the aqueous layer, the mixture was extracted six times with CH2Cl2 (12 mL). The combined organic layers were dried over anhydrous Na2SO4. Filtration and evaporation under reduced pressure gave crude amine,which was used without purification. All the crude corresponding amine was dissolved in dichloromethane (50 mL), and TCCA (trichloroisocyanuric acid) (3.2 g, 14 mmol) was added in a250 ml round-bottom flask at 0 C. Then, the mixture was stirred at ambient temperature during 1 h. Triethylamine (6.0 g, 6 mol) dissolved in dichloromethane (50 mL) was added, and the resulting mixture was washed with water (200 mL) and hydrochloric acid (1 M, 200 mL)successively. The organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, purification by column chromatography on silica gel (n-hexane/EtOAc:40/1) afforded pure product.

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, 1-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chu, Benfa; Fang, Lili; Guo, Shan; Qi, Bing; Shi, Pengfei; Wang, Qi; Zhu, Jin; Tetrahedron Letters; (2020);,
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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromobenzo[c][1,2,5]thiadiazole

To a clear solution of B(C6F5)3 (0.050 g, 0.098 mmol) in CH2Cl2 (5 mL) was added a colorless solution of 4-bromo-benzo[2,1,3]thiadiazole (0.021 mg, 0.098 mmol) in CH2Cl2 (5 mL). The resulting yellow solution was allowed to stir for 30 minutes at room temperature. The solvent was removed in vacuo and the resulting solid washed with pentanes (2.x.10 mL) and dried under vacuum for 1 hour. The product was collected as a faint yellow solid. Recovered yield, 60 mg (85percent). Crystal’s suitable for X-ray diffraction were grown via slow diffusion of pentane into a concentrated solution of 4 in CH2Cl2. Upon addition of excess B(C6F5)3 (3 equivalents total) to 4, no change in the 1H or 19F spectrum was observed from 25 to -50° C. 1H NMR (CD2Cl2): delta 8.02 (d, 3JH-H=8 Hz, 1H, benzothiadiazole-p-CH), 7.71 (dd, 3JH-H=8 Hz, 3JH-H=8 Hz, 1H, benzothiadiazole-m-CH), 7.50 (d, 3JH-H=8 Hz, 1H, benzothiadiazole-o-CH). {1H} NMR (CD2Cl2): delta -5.5 (bs). 13C{1H} NMR (CD2Cl2, -50° C.) partial: 152.79, (s, quaternary), 149.22 (s, quaternary), 148.90 (dm, 1JC-F=250 Hz, CF), 148.22 (dm, 1JC-F=250 Hz, CF), 146.55 (dm, 1JC-F=245 Hz, CF), 141.73 (dm, 1JC-F=245 Hz, CF), 140.85 (dm, 1JC-F=250 Hz, CF), 138.99 (dm, 1JC-F=240 Hz, CF), 137.05 (dm, 1JC-F=245 Hz, CF), 136.74 (s, benzothiadiazole-m-CH), 134.01 (s, benzothiadiazole-p-CH), 131.90 (dm, 1JC-F=250 Hz, CF), 117.22 (quaternary), 116.05 (s, benzothiadiazole-o-CH). 19F NMR (CD2Cl2): delta -125.2 (br, 1F, ortho-C6F5), -131.0 (br, 3F, ortho-C6F5), -135.2 (br, 1F, ortho-C6F5), -137.2 (br, 1F, ortho-C6F5), -154.5 (s, 1F, para-C6F5), -156.5 (br, 2F, para-C6F5), -161.6 (br, 2F, meta-C6F5), 163.8 (br, 4F, meta-C6F5). 19F NMR (CD2Cl2, -50° C.): delta -125.17 (m, 1F, 3JF-F=22 Hz, ortho-C6F5), -130.58 (m, 1F, 3JF-F=21 Hz, ortho-C6F5), -131.42 (m, 2F, 3JF-F=24 Hz, ortho-C6F5), -134.13 (m, 1F, 3JF-F=24 Hz, ortho-C6F5), -137.58 (m, 1F, 3JF-F=24 Hz, ortho-C6F5), -153.99 (m, 1F, 3JF-F=20 Hz, para-C6F5), -155.31 (m, 1F, 3JF-F=20 Hz, para-C6F5), -157.27 (m, 1F, 3JF-F=22 Hz, para-C6F5), -161.28 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -162.91 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -162.74 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -163.33 (m, 1F, 3JF-F=20 Hz, meta-C6F5), -163.77 (m, 1F, 3JF-F=22 Hz, meta-C6F5), -164.03 (m, 1F, 3JF-F=22 Hz, meta-C6F5). UV-vis: lambdamax=355 nm. X-Ray: C24H3B1Br1F15N2S1. Space Group=P-1. Cell: a=10.82(15) , b=11.82(18) , c=12.36(18) , alpha=63.7(3)°, beta=75.1(3)°, gamma=84.1(4)°, V=1369(35) 3. R=0.0432percent, Rw=0.1132percent. GOF=1.027.

According to the analysis of related databases, 22034-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bazan, Guillermo C.; Welch, Gregory C.; Coffin, Robert; Peet, Jeff; US2011/28656; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route 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.

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (7.4 g, 37 mmol) in HC(OMe)3 (100 mL) was added TsOH (0.36 g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4, and concentrated. The crude product was used in next step without further purification (7.3 g, 93%). LCMS (mlz): 212.1 (M+ 1).

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

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 6274-57-3,Some common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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.

a) 4-(4-Dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal To a solution of 36.4 g (0.17 mol) of 4-bromo-N,N-dimethylbenzylamine in 250 ml of dry tetrahydrofuran, cooled to -70 C., are added dropwise, under a nitrogen atmosphere and with stirring, 112 ml (0.179 mol) of a 1.6 molar solution of n-butyllithium in hexane in such a way that the temperature does not exceed -65 C. The orange solution is stirred for a further 15 minutes at -70 C. and then within 10 minutes a solution of 27.6 g (0.172 mol) of 1,4-cyclohexanedione-monoethylene ketal in 110 ml of tetrahydrofuran is added, whilst the temperature must not exceed -65 C. The reaction mixture is stirred first for 30 minutes at -70 C. and then without external cooling until a temperature of +20 C. is reached, then poured into 600 ml of ice water and extracted with 200 ml of ethyl acetate. The organic phase is separated off and the aqueous phase is extracted several times with ethyl acetate. The combined organic extracts are dried with sodium sulphate, evaporated down in vacuo and the residue remaining is recrystallized from diisopropylether. 41.9 g (85% of theory) of 4-(4-dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal are obtained, m.p. 84-86 C.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Karl Thomae GmbH; US5726205; (1998); 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. 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Bromo-4-fluoro-2-methylaniline

The starting 5-bromo-4-fluoro-2-methylaniline (1) (20 g, 98 mmol) was dissolved in anhydrous 1-methylpyrrolidinone (100 mL), and copper (I) cyanide (17.6 g, 196 mmol) was added. The reaction was heated to 180 C. for 3 hours, cooled to room temperature, and water (300 mL) and concentrated ammonium hydroxide (300 mL) added. The mixture was stirred for 30 minutes and extracted with EA (3*200 mL). The combined extracts were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The oily residue was washed with hexanes (2*100 mL), and the solid dissolved in dichloromethane and loaded onto a silica gel column. Eluting with 0 to 25% EA in hexanes gradient provided 5-amino-2-fluoro-4-methylbenzonitrile (10.06 g, 67.1 mmol). LC/MS (m/z: 151 M+1).

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 627871-16-3.

Reference:
Patent; Gilead Sciences, Inc.; Notte, Gregory; US2013/197037; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, 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 54962-75-3, Formula: C7H5BrF3N

Add propylene oxide (36 mg, 0.624 mmol) and lithium perchlorate (56 mg, 0.458 mmol) to the solution of 3-bromo-5-(trifluoromethyl)aniline (100 mg, 0.416 mmol) in acetonitrile (5 mL), stir the resulting mixture overnight at ambient temperature. Upon completion of the reaction, concentrate the mixture under reduced pressure. Purify the residue by flash chromatography (silica gel, PE_EtOAc=5:l) to afford the product (136 mg, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Step 1 : To a stirred solution of (4-bromo-2-fluorophenyl)methanamine (2.5 g, 12.25 mmol) in pyridine (10 mL) at 0 C in a protective gas atmosphere was added methanesulfonyl chloride (1 .422 mL, 18.38 mmol) slowly in portions. After addition, the suspension was stirred at 0 C for 1 h. The reaction mixture was diluted with ice cold water (20 mL) and pH was adjusted to ~1 using 16 % aqueous HCI solution. The resulting precipitation was filtered off, washed with ethyl acetate (3 x 20 mL) and dried overnight. The crude N-(4-bromo-2-fluorobenzyl)- methanesulfonamide (3.14 g, 91 %) was used as such without further purification.

The synthetic route of 112734-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/45451; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 22385-77-9, 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 22385-77-9 as follows.

In a 500mL dry three-necked bottle, Compound 9 (23.8 g, 0.1 mol) was first dissolved in 200 mL of dry tetrahydrofuran. The flask was placed at -10 ° C. Compound 10 was slowly added (26.9 g, 0.1 mol) And t-BuLi (60 mL, 1 M in THF, 60 mmol), The reaction was carried out for 20 h under a nitrogen atmosphere. After the reaction, water is added to quench the reaction. Then with ethyl acetate, Water extraction reaction, Dry over anhydrous sodium sulfate, Concentrated under reduced pressure, Further column chromatography gave Compound 8 (21 g, 50percent).

According to the analysis of related databases, 22385-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wanhua Chemical Group Co., Ltd.; Wang Zesheng; Cong Xin; He Guangwen; Liu Chao; Dong Ke; Wang Peng; Cui Qian; Yu Yanbing; (12 pag.)CN109134538; (2019); A;,
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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H18Br2

General procedure: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary