Month: May 2021

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. 137-43-9, name is Cyclopentylbromide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H9Br

General procedure: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 × 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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 137-43-9.

Reference:
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 117635-21-9, 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. 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In the reaction vessel, 1,4-dibromo-2,5-dihexylbenzene (0.81 g, 2.0 0 mmol),20 ml of tetrahydrofuran was added, and at -78 C.,The mixture was stirred. Thereafter, 1.6 M n-butyllithium (n-BuLi) hexane solution (2.53 ml, 4.00 mmol) was added dropwise and after stirring for 1 hour, 3,5-diphenyl- 1-chlorotriazine was added , And the mixture was stirred at room temperature for 3 hours.After completion of the reaction, water was added to the reaction mixture,The mixture was extracted with chloroform, and the organic layer was concentrated. after that,Tetrahydrofuran was added to and dissolved in the resulting residue,Purification was carried out by reprecipitation twice using methanol to obtain a compound B.

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

Reference:
Patent; SAMSUNG ELECTRONICS COMPANY LIMITED; SHIBATA, KATSUNORI; ISHII, HIROTO; MOTOYAMA, TAKAO; (23 pag.)JP2016/108255; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 20027-95-6, name is 1,5-Dibromo-2,6-dimethylnaphthalene, 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 20027-95-6, category: bromides-buliding-blocks

(1) Synthesis of Intermediate C Intermediate C was synthesized according to the following scheme. In argon atmosphere, 17 g of 1,5-dibromo-2,7-dimethylnaphthalene, 35 g of bispinacolate diboron, 2.8 g of Pd(dppf)Cl2, 22 g of potassium acetate, and 400 ml of DMF were charged into a flask. The mixture was heated under stirring at 80 C for 65 h. After cooling, the precipitate was collected by filtration, washed with water and then toluene, and dried. Then, a mixture of 15 g of the obtained boronic ester, 27 g of bromoiodobenzene, 1.9 g of tetrakis(triphenylphosphine), 26 g of sodium carbonate, 120 ml of water, and 420 ml of DME in a flask was heated under stirring in argon atmosphere at 78 C for 665 h. After cooling, the precipitate was collected by filtration, washed with water and then methanol, and recrystallized from toluene. Then, a mixture of 13 g of the obtained dibrominated compound and 120 ml of pyridine in a flask was heated to 95 C. Thereafter, 10 g of potassium permanganate and 10 ml of ion exchanged water were added to the mixture. Then, 13 portions of 2 g of potassium permanganate and 2 ml of water were added to the mixture every ten minutes. The reaction product solution was hot-filtered and the filtrate was neutralized by a 2 N hydrochloric acid. The precipitated white solids were collected by filtration and washed with water. Finally, a mixture of 15 g of the obtained dicarboxylic compound and 300 ml of a concentrated sulfuric acid in a flask was heated under stirring at 85 C for 3 h. After cooling, the reaction product solution was slowly added to iced water, and the precipitated solids were collected by filtration and washed with ion exchanged water. The solids were further purified by sublimation, to obtain 7 g of the intermediate C. Through IR measurement of the obtained compound, it was found that the absorption attributable to carbonyl group appeared at 1720 cm-1. Mass spectrometric measurement showed a peak at M/Z = 802.

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, 1,5-Dibromo-2,6-dimethylnaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2371812; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 376646-62-7, 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. 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (4-bromo-2-methylphenyl)methanamine (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc2O (1.43 g, 6.6 mmol). The mixture was stirred at rt for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H): 300.1.

The chemical industry reduces the impact on the environment during synthesis (4-Bromo-2-methylphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; HUMORA, Michael; (306 pag.)WO2016/201280; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 41825-73-4, 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 41825-73-4 as follows.

lc N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide.; 2-Bromo-4,6-dimethyl-aniline (600 mg) and (4-fluoro-phenyl)-acetyl chloride (543 mg) were dissolved in acetonitrile (6 mL) and heated to 150 C for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0 0C, the product filtered off and washed with cold acetonitrile (50 mL) affording 665 mg (66% yield) of the title compound as a white solid. LC-MS (m/z) 337 (MH+); tR = 2.93, (UV, ELSD) 90%, 98%. 1H NMR (500 MHz, DMSOd6): 2.05 (s, 6H), 2.25 (s, 3H), 3.63 (s, 2H), 7.05 (b, IH), 7.15 (dt, 2H), 7.32 (b, IH), 7.40 (dt, 2H), 9.67 (s, IH).

According to the analysis of related databases, 41825-73-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; WO2006/29623; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 117635-21-9, 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. 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In the dry box the mixture of boronic acid pinacol ester,3, (5.6g, 16.82mmol), 1 ,4-dibromo-2,5-dihexylbenzene (3.4g, 8.4mmol), Aliquat 336 (0.8g), and Pd(PPh3) (0.486g, 0.421 mmol) in degassed toluene (100ml_) was prepared. Outside dry box, the degassed Na2CO3 (2.67g, 25.23mmol in 50 ml_ of water) solution was added to the former mixture under nitrogen, and then the resultant mixture was stirred at 90C for 42hrs. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4. Filtration, concentration of the filtrate, and then the silica column chromatography (0-3% ethyl acetate in hexane) provided the desired product (2.1 1 g, 38% yield) as a viscous liquid. This diboc-protected material was deprotected by the overnight reaction at room temperature with TFA solution (5ml_ of TFA in 50ml_ of DCM). The reaction mixture was concentrated under reduced pressure followed by the neutralization with saturated NaHCO3. Ethyl acetate extraction, drying over anhydrous MgSO4, concentration of the organic layer under reduced pressure, then silica column chromatography (30% ethyl acetate in hexane) provided the desired diamine material,7, (1 .16g, 80% yield) as a viscous liquid.

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; PARK, Kyung-Ho; RADU, Nora, Sabina; JOHANSSON, Gary, A.; FENNIMORE, Adam; DELANEY, William, J.; LECLOUX, Daniel, David; WO2011/159872; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1123172-38-2, name is 1-Bromo-3-(tert-butyl)-5-fluorobenzene, 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 1123172-38-2, category: bromides-buliding-blocks

3-tert-Butyl-5-fluoro-benzaldehyde (Example 21b) To a solution of 1-bromo-3-tert-butyl-5-fluoro-benzene (1.04 g, 4.5 mmol) in anhydrous THF (25 mL) is added under argon a 2.5M solution of nBuLi in hexane (1.9 mL, 4.7 mmol) at -78 C. After stirring for 0.5 h at -78 C. DMF (0.7 mL, 9 mmol) is slowly added by syringe, and the mixture is stirred again for 1.5 h at -78 C. The reaction mixture is added to 0.5N HCl and extracted with Et2O. The product obtained as a light yellow solid is suitable for use in the next step: TLC (hexane-EtOAc 1:1) Rf=0.36; HPLC RtA=2.08 min; 1H-NMR (400 MHz, CDCl3): delta 9.95 (s, 1H), 7.69 (m, 1H), 7.36 (m, 2H), 1.38 (s, 9H). c) 3-tert-Butyl-5-fluoro-benzaldehyde; To a solution of 1-bromo-3-tert-butyl-5-fluoro-benzene (1.04 g, 4.5 mmol) in anhydrous THF is added under Argon at -78 C. 2.5 M nBuLi in hexane (1.9 mL, 4.7 mmol) and after stirring for 0.5 h at -78 C. DMF (0.70 mL, 9 mmol) is added. After stirring for 1.5 h at -78 C. the reaction mixture is added to 0.5 N aqueous HCl and extracted with Et2O. Combined organic layers are washed with brine, dried over MgSO4, filtered and evaporated. The title compound is obtained as a light yellow oil and is used a s such for the next transformation: TLC (hexane-EtOAc 10:1) Rf=0.36; HPLC RtA=2.08 min; 1H-NMR (400 MHz, CDCl3): delta 9.98 (s, 1H), 7.68 (s, 1H), 7.36 (m, 1H), 1.25 (s, 9H).

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; Briard, Emmanuelle; Lueoend, Rainer Martin; Machauer, Rainer; Moebitz, Henrik; Rogel, Olivier; Rondeau, Jean-Michel; Rueeger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2009/54427; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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.

In a 10 mL vial charged with [l-[(4,4-difluorocyclohexyl)methyl]-6-(3,5-dimethylisoxazol-4-yl)pyrrolo[3,2-b]pyridin-3- yl]boronic acid (51, 0.05 g, 0.13 mmol) and acetonitrile (4 ml) was added l-bromo-4- (difluoromethyl)benzene (0.05 g, 0.24 mmol), 1M aqueous potassium carbonate (2 ml), and [1, 1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.01 g, 0.01 mmol). The reaction mixture was heated at 140 C in a microwave reactor for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine. Then, the organic layer was dried over magnesium sulfate and the drying agent removed by filtration. The volatiles were removed from the filtrate under reduced pressure and the crude material was purified by silica gel flash chromatography eluting with 0-50% ethyl acetate in hexane to provide product as a tan solid (P-0608, 18 mg, 28.6%) MS (ESI) [M+H+]+ = 472.0.

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; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 6320-40-7, A common heterocyclic compound, 6320-40-7, name is 1,3,5-Tribromo-2-methylbenzene, molecular formula is C7H5Br3, 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.

In a 100 mL agate ball mill jar, 3.29 g (10 mmol)2,4,6-tribromotoluene, 0.0010 g (0.0010 mmol) 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin cobalt (II), 6.44 g (50 mmol) 70% t-butyl hydroperoxide aqueous solution and 16.45 g of anhydrous sodium sulfate were mixed uniformly, and the ball mill tank was sealed. At room temperature, the ball milling reaction was performed at a speed of 800 rpm for 16.0 h, and the ball milling was stopped every 1.0 h to release the gas in the ball milling tank. After completion of the reaction, the obtained reaction mixture was dissolved in 30 mL of absolute ethanol and stirred at room temperature for 30.0 min. Filter, wash the obtained filter cake with 2 × 10 mL of absolute ethanol, combine the ethanol solutions, and make the resulting ethanol solution to 100 mL. 20 mL of the obtained solution was removed, desolvated under reduced pressure, and the obtained reaction mixture was separated by column chromatography (V cyclohexane: V ethyl acetate = 4: 1 to 1: 4). The conversion of 2,4,6-tribromotoluene was 31%, and the selectivity of 2,4,6-tribromobenzoic acid was 99%. No other significant oxidation products were detected.

The synthetic route of 6320-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Shen Haimin; Qi Bei; She Yuanbin; (18 pag.)CN110563590; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 41825-73-4,Some common heterocyclic compound, 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, molecular formula is C8H10BrN, 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 argon atmosphere, to a solution of 13.9 g (69.5 mmol) of2-bromo-4,6-dimethylaniline in 200 ml of THF, 27.9 ml of 2.5 M (69.5 mmol) “BuLi in hexanes were added at -5O0C. This mixture was stirred for 2 hours at ambient temperature. The resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 15.0 g (69.5 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-l-yl)silane in 100 ml of THF at O0C. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue 100 ml of toluene were added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 180-184C/0.5 mm Hg. Yield 20. I g (77%).Anal. calc. for C19H28BrNSi: C, 60.03; H, 7.46. Found: C, 60.25; H, 7.40.1H NMR (CDCl3): delta 7.15 (s, IH3 3-H in phenyl), 6.82 (s, IH, 5-H in phenyl), 3.10 (br.s, IH, 1-H in Cp), 2.95 (br.s, IH, NH), 2.22 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.01 (s, 6H, 2,5-Me in Cp), 1.83 (s, 6H, 3,4-Me in Cp), 0.15 (s, 6H, SiMe2).13C NMR (CDCl3): delta 140.8, 136.5, 132.7, 131.1, 130.8, 130.7, 130.3, 118.4, 56.3, 20.5, 20.1, 14.5, 11.3, -0.6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4,6-dimethylaniline, its application will become more common.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS, INC.; WO2007/70040; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary