Month: June 2021

Reference of 553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

K3PO4 (212 mg, 1 mmol),aryl halides (0.5mmol) and phenylboronicacid (0.75 mmol) were added successively into a dried Schlenk tubewith a magnetic bar under nitrogen. Then a N,N-dimethylacetamide (DMA 0.05 mL) solution of tetraphosphine TPPDA (0.0005 mmol) andPdCl2 (0.0005 mmol), which was reacted at 100 C for 1 h prior to use,was added into the mixture. Afterwards, o-xylene (3 ml) was addedwith syringe. After being stirred for the required time in the preset con-ditions, the reaction mixture was cooled to room temperature. The mix-ture solution was extracted with ethyl acetate (3 5 mL). Combinedorganic phase was washed with brine (3 5 mL) and dried over anhy-drous MgSO4. The dried solution was ltered and puried by silica gelchromatography (petroleum ether 60-90 C) to give a correspondingproduct. Reaction condition: aryl halides 0.5 mmol, phenylboronic acid 0.75 mmol, K3PO4 1.0mmol, o-xylene 3 mL, catalyst PdCl2/TPPDA = 1/1, 90 C, under nitrogen, GC yields.

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

Reference:
Article; Guo, Fei-Chen; Zhou, Rong; Jiang, Zhi-Jie; Wang, Wei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 66; (2015); p. 87 – 90;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3-Bromo-5-(trifluoromethyl)aniline

To a solution of 3-Amino-5-bromobenzotrifluoride (200mg) in pyridine (2mL) was added methane sulphonyl chloride (115mg) and one crystal of 4-(dimethyl- amino) pyridine. The mixture was stirred at room temperature for four hours then diluted with ethyl acetate (50mL) and washed with HCI .(2M, 50mL) and saturated sodium chloride solution (50mL). Organics were separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield N-(3- bromo-5-trifluoromethyl-phenyl) -methanesulfonamide (264mg). ¹H NMR (MeOD); 6 7.59 (s, 1 H), 7.58 (s, 1 H), 7.40 (s, 1 H), 7.00 (s, 1 H), 3.11 (s, 3H). MS m/z 318.9 (M+1).

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AKZO NOBEL N.V.; WO2005/121106; (2005); 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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C7H7BrFN

Step c) 2-[(4-Bromo-2-fluorophenyl)methyl]-1,2,3,4-tetrahydro-1,3-dioxo-4-isoquinolinecarboxylic Acid Methyl Ester To a solution of 3-methoxyl-1-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester (5.0 g, 21.37 mmol) in DMF (100 mL) were added 4-bromo-2-fluorobenzylamine (4.36 g, 21.37 mmol) and Et3 N (5.96 mL, 42.74 mmol). The mixture was stirred at 80 C. for 30 minutes, poured into H2 O (1500 mL), acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/hexane (after cooling to -20 C.) gave a white solid (7.6 g, 87.7%, m.p. 149-150 C.). 1 H NMR (DMSO-d6, 400 MHz): delta [3.67 (s), 4.0 (s), 3H, –CO2 Me, tautomeric], [5.06 (q), J=15.4 Hz, 5.30 (s), 2H, –NCH2 –, tautomeric], 5.4 (s), 1H, CH–CO2 Me, tautomeric], 7.07-8.43 (m, 7H, Ar–H, tautomeric). IR (KBr, cm-1): 1670 (CO), 1605 (CO). MS (+FAB): 406 (80, M+ +H), 374 (40, M+ –OCH3). Anal. Calcd.: C, 53.22; H, 3.23; N, 3.45. Found: C, 53.19; H, 2.98; N, 3.4.

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; American Home Products Corporation; US5068332; (1991); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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 955959-84-9, COA of Formula: C18H11BrO

In this example, a method for synthesizing N-(l, r-biphenyl-4-yl)-N-[4-(dibenzofuran-4-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-ami ne (abbreviation: FrBBiF-II) represented by Structural Formula (100) will be described. [0238] [0239] First, 2.1 g (6.6 mmol) of 4-(4-bromophenyl)dibenzofuran, 2.4 g (6.7 mmol) of N-(l,l ‘-biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine, and 1.9 g (20 mmol) of sodium tert-butoxide were put in a 200-mL three-neck flask and the air in the flask was replaced with nitrogen. To this mixture, 33 mL of toluene, 0.30 mL of a 10 % hexane solution of tri(ter/-butyl)phosphine, and 48 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0) were added, and stirring was performed at 90 C for 7.5 hours. After the stirring, suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531 – 16855), and alumina was carried out to give a filtrate. The filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (the developing solvent was hexane and toluene in a ratio of 3:1) to give a solid. The solid was recrystallized from toluene and hexane, so that 3.2 g of an objective solid was obtained in a yield of 81 %. A reaction scheme of this reaction is shown below. [0240] [0241] Using a train sublimation method, 1.0 g of the obtained solid was purified by sublimation. In the purification by sublimation, the pressure was 2.6 Pa, the flow rate of argon gas was 5.0 mL/min, and the temperature of the heating was 289 C. After the purification by sublimation, 0.99 g of a solid which was the object of the synthesis was obtained at a collection rate of 95 %. [0242] Results of measurement of the obtained solid by nuclear magnetic resonance ( NMR) are shown below. NMR (CDCI3, 500 MHz): delta = 1.46 (s, 6H), 7.18 (dd, J = 8.5 Hz, 2.5 Hz, 1 H), 7.26-7.48 (m, 14H), 7.53-7.56 (m, 2H), 7.60-7.68 (m, 6H), 7.86-7.91 (m, 3H), 7.99 (d, J = 7.5 Hz, 1 H). [0243] Thermogravimetry-differential thermal analysis (TG-DTA) of the obtained FrBBiF-II was performed. The measurement was conducted by using a high vacuum differential type differential thermal balance (TG/DTA 2410SA, manufactured by Bruker AXS Kappa.Kappa.)· The measurement was carried out under a nitrogen stream (a flow rate of 200 mL/min) and a normal pressure at a temperature rising rate of 10 C/min. The relationship between weight and temperature (thermogravimetry) shows that the 5 % weight loss temperature is 393 C, which is indicative of high heat resistance. [0244] FIGS. 13A and 13B are NMR charts. Note that FIG. 13B shows an enlarged part of FIG. 13A in the range of 7.00 ppm to 8.25 ppm. The measurement results confirmed that N-(l, -biphenyl-4-yl)-N-[4-(dibenzofuran-4-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-ami ne (abbreviation: FrBBiF-II), which was the target substance, was obtained. [0245] Physical Properties of FrBBiF-Il FIG. 14A shows an absorption spectrum and an emission spectrum of FrBBiF-II in a toluene solution of FrBBiF-II, and FIG. 14B shows an absorption spectrum and an emission spectrum of a thin film of FrBBiF-II. The spectra were measured with a UV-visible spectrophotometer (V550, produced by JASCO Corporation). The spectra of FrBBiF-II in the toluene solution of FrBBiF-II were measured with a toluene solution of FrBBiF-II put in a quartz cell. The spectra of the thin film were measured with a sample prepared by deposition of FrBBiF-II on a quartz substrate by evaporation. Note that in the case of the absorption spectrum of FrBBiF-II in the toluene solution of FrBBiF-II, the absorption spectrum obtained by subtraction of the absorption spectra of the quartz cell and toluene from the measured spectra is shown in the drawing and that in the case of the absorption spectrum of the thin film of FrBBiF-II, the absorption spectrum obtained by subtraction of the absorption spectrum of the quartz substrate from the measured spectra is shown in the drawing. [0246] As shown in FIG. 14A, in the case of FrBBiF-II in the toluene solution, an absorption peak was observed at approximately 360 nm, and an emission wavelength peak was observed at approximately 415 nm (excitation wavelength: 366 nm). As shown in FIG. 14B, in the case of the thin film of FrBBiF-II, absorption peaks were observed at approximately 368 nm, 294 nm, 266 nm, 247 nm, and 209 nm, and an emission wavelength peak was observed at approximately 428 nm (excitation wavelength: 376 nm). Thus, it was found that absorption and light emission of FrBBiF-II occur in extremely short wavelength regions. [0247] The ionization potential of FrBBiF-II in a thin film state was measured by photoelectron spectroscopy (the measuring instrument: AC-2, manufactured by Riken Keiki, Co., Ltd.) in the air. The obtained value of the ionization potential was converted into a negative value, so that the HOMO level of FrBBiF-II was determined to be -5.61 eV. From the da…

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; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; OGITA, Kaori; SEO, Satoshi; SEO, Hiromi; TAKAHASHI, Tatsuyoshi; WO2014/157018; (2014); 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-5-fluoroaniline

2-Bromo-5-fluoro-N-(propan-2-yl)aniline E-1.7″” ‘ 2-bromo-5-fluoroaniline E-1.7″”” (2.00 g; 10.53 mmol) is suspended in 20 ml DCM and propan-2-one (1.55 ml; 21.05) is added and the reaction mixture is stirred for 16 at 20°C. Afterwards sodium triacetoxyborohydride (4.69 g; 21.05 mmol) is added and the reaction mixture is stirred for 48h at 20 °C. The reaction mixture is poured into water and extracted with DCM. The combined organic layer is dried over MgS04 the solid materials are filtered off and HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. The crude product is purified using reversed phase chromatography (Method: prep. HPLC1). Product containing fractions are combined and extracted with DCM. To the organic layer HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. Yield 91percent (2.57 g; 9.58 mmol) HPLC-MS: tRet = 1.09 min; method VAB

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 1003-99-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58971-11-2, name is 3-Bromophenethylamine, 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 58971-11-2, Quality Control of 3-Bromophenethylamine

General procedure: Toa solution of 2a (20.0 g, 0.1 mol)and triethylamine (30.3 g, 0.3 mol) in DCM (350 mL) was added ethylchloroformate (12.9 g, 0.1 mol) dropwise at 0 oC and then stirred atroom temperature for 3 h. The reaction mixture was washed with 3M HCl (100 mL×2), dried over Na2SO4 and concentrated under reducedpressure. The residue was purified by silica gel column chromatography (PET/EA= 25:1, v/v) to afford compound 3a as colorless oil (22.3 g, 82.0%).

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

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route 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.

1-bromo-3-(tertbutyl)benzene (300 mg, 1.41 mmol) was dissolved in dry THF (5 mL) at -78 C under nitrogen and was stirred for 10 min. n-BuLi (2.5 M in hexanes, 2.0 mL, 4.9 mmol) was added drop wiseto the solution was stirred for 2 h at -78 C. After two hours, ethyl fluoroacetate (0.16 mL, 1.69mmol) was added drop wise and stirred for 1 min at -78 C upon which the mixture was then quenched with NH4Cl (20 mL) and warmed to room temp. The mixture was then extracted withether (50 mL), and dried over MgSO4. After concentration in vacuo (note: remove shortly afterthe ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (hexane: ethyl acetate = 90:10) to yield the product as a yellowliquid in 43percent yield (0.12 g).

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

Reference:
Article; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
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. 858121-94-5, name is 4-(Bromomethyl)-1,1-difluorocyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(Bromomethyl)-1,1-difluorocyclohexane

General procedure: DIPEA (778 muIota, 4.46 mmol) was added dropwise to a stirred solution of N-(2-hydroxyethyl)-4- (2H-tetrazol-5-yl)benzenesulfonamide (300 mg, 1.1 14 mmol, Intermediate 17′) and 2- (bromomethyl)tetrahydro-2H-pyran (285 muIota, 2.228 mmol, commercial source: Aldrich) in N,N- Dimethylformamide (DMF) (3714 muIota) at rt under nitrogen. The mixture was stirred at rt for 3 days. As starting material remained, it was stirred at 70 C overnight. The mixture was concentrated under reduced pressure. The crude compound was purified by flash column chromatography (silica; EtOAc-cyclohexane from 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to obtain the product as a racemic mixture N-(2- hydroxyethyl)-4-(2-((tetrahydro-2H-pyran-2-yl)methyl)-2H-tetrazol-5-yl)benzenesulfonamide (49 mg, 0.133 mmol, 28%). NMR (400 MHz, Acetone-d6) delta 7.84-7.78 (m, 2H), 7.56-7.50 (m, 2H), 7.33 (t, J = 5.9 Hz, 1 H), 4.37-4.32 (m, 2H), 4.25 (t, J = 5.6 Hz, 1 H), 3.50-3.44 (m, 1 H), 3.38-3.32 (m, 1 H), 2.94-2.90 (m, 2H), 2.86-2.80 (m, 1 H), 2.41-2.37 (m, 2H), 1.40-1.25 (m, 2H), 1.12-0.85 (m, 4H). MS m/z [M-H]”= 366.2

According to the analysis of related databases, 858121-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-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. Computed Properties of C9H12BrN

Dimethylamine 49 (1.31 g, 6.13 mmol) was dissolved in anhydrous THF (15 ml) under Ar(g) in a flame-dried round-bottomed flask equipped with a reflux condenser. To facilitate generation of the Grignard reagent, a catalytic amount of 12 was added to the solution. Crushed magnesium turnings (223 mg, 9.2 mmol) were then added to this solution, and the resulting solution was heated at reflux for 2 hr to generate the Grignard reagent. In a separate flamed-dried flask, diethyl phosphite (237 mul, 1.84 mmol) was dissolved in anhydrous THF (1.0 ml), and cooled to 0 C. with an ice bath. The solution of Grignard reagent was added dropwise to this solution, and the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then quenched with water (1 ml), and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the resulting solution was washed with water and brine. The combined organic extracts were dried over anhydrous MgSO4(s) and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% v/v MeOH in CH2Cl2) to give phosphine oxide 50 as a colorless oil in 66% yield. 1H NMR (CDCl3, 400 MHz) delta 8.06 (d, J=1.2 Hz, 1H), 7.69 (s, 1H), 7.66 (s, 1H), 7.58 (t, J=7.5 Hz, 2H), 7.54 (dd, J=8.9, 1.2 Hz 2H), 7.45 (dd, J=7.6, 3.1 Hz 2H), 3.45 (s, 4H), 2.22 (s, 12H) ppm; 13C NMR (CDCl3, 100.6 MHz) delta 140.22 (d, J=10.7 Hz), 133.45, 132.15, 131.31 (d, J=12.2 Hz), 129.67 (d, J=11.2 Hz), 129.14 (d, J=12.2 Hz), 64.06, 45.58 ppm; 31P NMR (CDCl3, 161 MHz) delta 22.02 ppm; MS (ESI) m/z 288.0393 (MH+[C18H25N2OPH+]=288.0383).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Wisconsin Alumni Research Foundation; Raines, Ronald T.; Tam, Annie; Soellner, Matthew B.; US8410247; (2013); B2;,
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. 7745-91-7, name is 3-Bromo-4-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8BrN

3-Bromo-4-methylaniline (30.4 g) was dissolved in methanol (210 mL), pyridine (43 mL) and iodine (68.4 g) were added, and the mixture was stirred at 25C for two hours. A 20% aqueous sodium thiosulfate solution (150 mL) and water (30 mL) were added to the reaction solution and the mixture was stirred at 25C for one hour. Washing with methanol/water (1/1, 100 mL) resulted in the target compound (19.1 g).

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; Chugai Seiyaku Kabushiki Kaisha; F. Hoffmann-La Roche AG; EBIIKE, Hirosato; AOKI, Toshihiro; CHIBA, Takashi; KOCHI, Masami; NAKAMA, Kimitaka; NIIZUMA, Satoshi; NISHII, Hiroki; OHWADA, Jun; SHIMAMURA, Hiroyuki; SUGE, Aiko; NAKANISHI, Yoshito; KOBAYASHI, Natsuki; (594 pag.)EP3312172; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary