Tag: M.W=200-300

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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

PREPARATION 47 4-(2,2-difluoro-1,3-benzodioxol-5-yl)aniline A solution of 5-bromo-2,2-difluoro-1,3-benzodioxole (2.65 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.97 mmol), tetrakis(triphenylphosphine)palladium(0) (0.08 mmol), and cesium carbonate (7.94 mmol) in N,N-dimethylformamide (8.0 mL) and water (2.0 mL) was heated at 100 C. for 18 h. The reaction mixture was cooled, poured into brine (60 mL), and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a white solid (50%). ESMS [M+H]+: 250.2.

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; Parrish, Cynthia A.; Dhanak, Dashyant; US2007/142460; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5003-71-4,Some common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, molecular formula is C3H9Br2N, 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 A N-Benzyloxycarbonyl-3-bromopropylamine To a stirred suspension of 3-bromopropylamine hydrobromide (2 g, 9.14 mM) in 40 mL dry THF was added, via hypodermic syringe, benzyl chloroformate (1.64 g, 9.60 mM) at room temperature. After cooling to 0 C., diisopropylethylamine (1.6 mL, 9.20 mM) was added dropwise via syringe and the reaction mixture was allowed to stir at 0 C. for 1 hour. The crude reaction mixture was filtered over a pad of Celite and solvents were evaporated. The residue was flash chromatographed on silica gel, eluding with 10-20-30% EtOAc/hexane to afford 1.56 g desired product as a liquid, homogeneous by TLC in 80:20 hexane-EtOAc; 1 H-NMR (200 MHz, CDCl3, ppm) delta2.06 (m, 2H), 3.37 (m, 4H), 4.92 (br, 1H), 5.10 (s, 2H), 7.34 (s, 5H). Mass spectrum (FAB) m/e 273 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromopropan-1-amine hydrobromide, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5411980; (1995); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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 52723-82-7, HPLC of Formula: C7H7BrFN

Acetic anhydride (1.488 mL, 15.77 mmol) was added to a suspension of 4-bromo-5- fluoro-2-methylaniline (1.6087 g, 7.88 mmol) in chloroform (18 mL) under ice-bath cooling and the mixture stirred at RT for 5 min. Potassium acetate (0.812 g, 8.28 mmol), a solution of 18-crown-6 (0.417 g, 1.577 mmol) In chloroform (4 mL) and then t-butyl nitrite (2.186 mL, 16.56 mmol) were then added and the mixture heated at 75°C for 16 h. The dark brown mixture was then cooled, DC (20 mL) added and the organic layer washed with saturated aqueous sodium bicarbonate solution (ca. 20 mL) then reduced. The residue was purified by chromatography on silica gel eluting with a gradient of 0-30percent ethyl acetate in hexane. Impure fractions were purified further by chromatography on silica gel eluting with a gradient of 0-20percent ethyl acetate in isohexane. All pure fractions were combined and then reduced to afford the title compound as a light orange solid (984 mg). 1H N R (CDCl3l 400MHz) delta ppm: 2.79 (3H, s), 7.95 (1 H, dd, 6.5 Hz, 0.5 Hz), 8.07 (1H, d, J 1.0 Hz), 8.25 (1 H, dd, J 9.0, 0.5 Hz).

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; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of bromo-tert- butylbenzene (4.62 g, 21.68 mmol) in THF (50 mL) was cooled to-78 °C then n- BuLi (2.5M, 9.1 mL) was added dropwise. The reaction was stirred for 30 min then a solution of 1-benzyl-piperidin-4-one (3.69 g, 19.5 mmol) in THF (10 mL) was added dropwise. After stirring for 30 min at-78 °C, the reaction was warmed to 0°C then quenched with water (50 mL). The reaction was diluted with ethyl acetate (100 mL); the organic was separated, washed with brine (50 mL), dried over magnesium sulfate and concentrated yielding an oil (6.94 g, 21.5 mmol), which was used in the next step without further purification; LC rt=2.98 min; MS (ESI) 306.2.

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (30 mL) was added dropwise to 3-bromopropan-1-aminium bromide (10.84 g, 50 mmol) in DCM (50 mL). After 15 min stirring, di-tert-butyl dicarbonate (21.8 g, 100 mmol) in DCM (40 mL) was added dropwise to the solution for 1 h, and the resulting mixture was stirred for 2 days at room temperature. The resulting solution was washed with 1 N aqueous HCl, water × 2, saturated aqueous NaHCO3, and brine. The organic phase was dried with Na2SO4, and thes olvent was removed in vacuo to give tert-butyl (3-bromopropyl) carbamate (20.54 g, yield = 88%).

The chemical industry reduces the impact on the environment during synthesis 3-Bromopropan-1-amine hydrobromide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qin, Huihuan; Li, Lingling; Li, Kun; Xiaoqi, Yu; Chinese Chemical Letters; (2019); p. 71 – 74;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1137142-58-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1137142-58-5 name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 23; lmidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine; A mixture of 2-bromo-imidazo[2,1-b][1 ,3,4]thiadiazole (1.0 g, 4.90 mmol) and p- anisidine (19.6 mmol, 2.41 g) in trifluoroethanol (12 mL) was heated under microwave irradiation at 170C for 1 hour. On cooling, the mixture was diluted with dichloromethane (10 mL) and purified by column chromatography (Biotage/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1 :9). The residue obtained was triturated with diethylether and few drops of methanol to give imidazo[2,1-b][1 ,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine as a white solid (355 mg, 29% yield). 1H-NMR (300 MHz, CDCI3): delta 8.01 (s, 1 H), 7.55 (s, 1 H), 7.44 (d, J = 8.9, 2H), 7.22 (s, 1H), 6.90 (d, J = 8.8, 2H), 3.80 (s, 3H). MS (ES+) m/z 247 (M+H)+ (MW: 246.29).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

B) Methyl (1RS,2SR)-2-(6-bromo-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylate [0305] O-(7-Azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (554 mg) was added to a solution of 4-bromo-N2-methylbenzene-1,2-diamine (279 mg), diisopropylethylamine (0.727 mL) and (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (200 mg) in DMF (5 mL) at room temperature. The mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was dissolved in acetic acid (5 mL), and the mixture was stirred at 80C for 1 hr. After concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (80 mg) as a pale brown solid. MS (ESI+):[M+H]+ 309.1. 1H NMR (400 MHz, DMSO-d6) delta 1.55 (1H, dt, J = 8.4, 4.3 Hz), 1.72-1.80 (1H, m), 2.26-2.36 (1H, m), 2.74 (1H, q, J = 8.4 Hz), 3.41 (3H, s), 3.72 (3H, s), 7.28 (1H, d, J = 8.5 Hz), 7.49 (1H, d, J = 8.5 Hz), 7.76 (1H, s).

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; Takeda Pharmaceutical Company Limited; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; KINA, Asato; EP2848621; (2015); 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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Compound B-3 (40 g, 161.9 mmol) was dissolved in acetic acid (200 mL). To this was added iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol), and sulfuric acid (10 mL) and the mixture was stirred at 65 C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and water was added thereto. The resulting solid was filtered, washed with water and then recrystallized with toluene and ethyl acetate to obtain 50.1 g (yield: 83%;

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Jeong Min-u; Lee Dong-hun; Park Tae-yun; Cho Seong-mi; Lee Jeong-ha; Lee Ju-yeong; (32 pag.)KR2018/76357; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 138526-69-9

(a) To 50 ml of N-methylpyrrolidone were added 10 g of 3,4,5-trifluorobromobenzene and 8.5 g of copper cyanide, and the resulting mixture was stirred at 150C for 4 hours. Thereafter, aqueous ammonia was added to the reaction mixture which had been allowed to cool to near room temperature, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 5.0 g of 3,4,5-trifluorobenzonitrile was obtained.

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2151432; (2010); 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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H6Br2N2

iert-butyl (1-(5,6-dibromo-1 H-benzo[d]imidazol-2-yl)-2-(4- methoxyphenyl)ethyl)carbamate: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-((terf-butoxycarbonyl)amino)-3-(4- methoxyphenyl)propanoic acid (500 mg, 1.69 mmol) in AcCN (16.9 mL) was treated at rt with 4-ethylmorpholine (0.43 mL, 3.39 mmol), TBTU (544 mg, 1.69 mmol) and 4,5- dibromobenzene-1 ,2-diamine (450 mg, 1.69 mmol). The reaction mixture was stirred at rt until completion. The reaction mixture was diluted with EA and water. The org. phase was dried over MgS04, filtered, and the solvent was removed under reduced pressure. The residue was dissolved in glacial acetic acid (25 mL) and the reaction mixture was stirred at 60 C for 1 h. The mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was partitioned between EA (25 mL) and sat. aq. NaHC03 (25 mL). The org. layer was washed with sat. aq. NaHC03 (twice 25 mL), dried over MgS04, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:6 EA-heptane) gave the title compound as beige solid: TLC: rf (4:6 EA-heptane) = 0.35. LC-MS-conditions 12: tR = 0.88 min; [M+H]+ = 525.61.

According to the analysis of related databases, 49764-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CORMINBOEUF, Olivier; CREN, Sylvaine; LEROY, Xavier; POZZI, Davide; WO2015/19325; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary