Month: March 2021

1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, 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. Recommanded Product: 1193389-40-0

Intermediate AN-(1-(4-bromophenyl)cyclobutyl)-4-(difluoromethoxy)benzenesulfonamideTo a solution of 1-(4-bromophenyl)cyclobutanamine, HCl (845 mg, 3.22 mmol) in DMF (10 mL), was added diisopropylethylamine (1.69 mL, 9.66 mmol) and 4-(difluoromethoxy)benzene-1-sulfonyl chloride (0.529 mL, 3.22 mmol). The reaction mixture was then stirred at r.t., overnight. This mixture was then used, as is, in the following experiment.

The synthetic route of 1193389-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2011/207749; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 C: 4-Amino-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (4) 4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (33.8 g, 208 mmol) was mixed with water (300 mL). At 60 C., 3-bromo-4-fluoroaniline (Sigma-Aldrich) (43.6 g, 229 mmol, 1.1 equiv.) was added to the suspension with stirring for 10 min. A solution of sodium bicarbonate (26.3 g, 313 mmol, 1.5 equiv.) in water (300 mL) was added over 15 min with stirring at 60 C. After stirring 20 min, LCMS indicated reaction completion. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2*300 mL). The combined ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to give the desired product (65 g, 99%) as an off-white solid, which was used in the subsequent reaction without further purification. C9H7BrFN5O2 (MW 316.09), LCMS (EI) m/e 316/318 (M++H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Tao, Ming; Frietze, William; Meloni, David J.; Weng, Lingkai; Zhou, Jiacheng; Pan, Yongchun; US2015/133674; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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. Application In Synthesis of 1,4-Dibromo-2,5-difluorobenzene

1,4-Dibromo-2,5-difluorobenzene (51.2 g, 188 mmol) was dissolved in 1,2-diethoxyethane (400 ml), and a 2.5 M n-butyllithium/ hexane solution (76.0 ml, 190 mmol) was slowly added dropwise thereto at -78 C. in the presence of nitrogen gas. [0674] After the reaction solution was stirred at -78 C. for 30 minutes, dry ice was added thereto, followed by stirring for further 30 minutes. After the temperature was gradually raised to room temperature, water (200 ml) was added to the reaction liquid. The reaction liquid was diluted with ethyl acetate, and washed with a 10% aqueous sodium carbonate solution (200 ml¡Á2). Then, the obtained aqueous layers were combined, and made acidic by adjustment with 1 N hydrochloric acid. The precipitated yellow solid was filtered and dried to obtain the title compound (30.0 g, 67%). [0675] 1H NMR (DMSO-d6, 400 MHz): delta 7.90-7.87 (m, 1H), 7.79-7.75 (m, 1H).; MS (ESI) m/z 191 (M+H-44)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 18648-66-3,Some common heterocyclic compound, 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, molecular formula is C20H15Br, 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.

(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannan (0.81 g 2.66 mmol), 1-bromo-4-(2,2-diphenylvinyl)benzene (a compound of the Chemical Formula 2r) (1.7 g, 3.2 mmol), and Pd(PPh3)4 (0.15 g, 0.13 mmol) were dissolved in toluene (40 ml), and then refluxed under nitrogen atmosphere for 8 hours. Subsequently, an organic layer was extracted with methylene chloride and water and distilled, and column chromatography was performed (eluent-MC:Hx=1:4) to synthesize a compound of the Chemical Formula 4r.1H NMR (CDCl3): [ppm]=4.68 (s, 2H), 4.72 (s, 2H), 6.71 (s, 1H), 6.96 (s, 1H), 7.08 (s, 1H), 7.18 (m, 4H), 7.40 (m, 2H), 7.48 (m, 6H), 7.56 (d, 3JHH=8.8 Hz, 2H).

The synthetic route of 18648-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongjin Semichem Co., Ltd.; US2011/94588; (2011); 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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., Safety of 4,6-Dibromodibenzo[b,d]furan

A mixture of 13 g (40 mmol) of 4,6-dibromobenzofuran, 11.3 g (40 mmol) of bis(4-tert-butylphenyl)amine, 0.9 g (0.8 mmol) of Pd2(dba)3, 1.2 g (0.6 mmol) of tri-tert-butylphosphine, 5.0 g (52 mmol) of sodium tert-butoxide, and 150 ml of toluene was placed under nitrogen, and then heated and stirred at 70 C. for 24 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. The solution was extracted with 100 ml of ethyl acetate and 300 ml of water. The organic layer was dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica to give product (16 g, 30.4 mmol, 76%).

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; LUMINESCENCE TECHNOLOGY CORPORATION; Yen, Feng-Wen; Chuang, Li-Chieh; Huang, Tsun-Yuan; (76 pag.)US2019/348609; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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 59907-13-0, Computed Properties of C7H6BrF

[0314] To a solution of 7-isopropyl-2-methyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2- yl) -pyrazolo[l,5-a]pyrimidine-5-carboxylic acid ethyl ester (120 mg, 0.32 mmol) and 2- bromo-l-fluoro-3-methyl-benzene (60.8 mg, 0.322 mmol) in toluene (3 mL) were added Pd(PPh3)4 (37.2 mg, 0.032 mmol) and K3P04 (273.4 mg, 1.28 mmmol). The resulting mixture was bubbled with N2 for 5 mins and stirred at 130 C irridiated by microwave for 2 hrs. Then the reaction mixture was filtered, and the filtrate was concentrated in vacuum to give a residue, which was purified by a reversed-phase column (B from 5-95, A: H20, B: ACN) to afford 3-(2-fluoro-6-methyl-phenyl) -7-isopropyl-2-methyl-pyrazolo[l,5- a]pyrimidine-5-carboxylic acid ethyl ester (30.0 mg, yield: 26%) as a yellow solid. [0315] 1HNMR (400 MHz, CD3OD): delta = 7.46 (s, 1H), 7.37-7.31 (m, 1H), 7.18 (d, J = 7.6 Hz, 1H), 7.04 (t, J= 8.8 Hz, 1H), 4.44-4.39 (m, 2H), 3.96-3.92 (m, 1H), 2.37 (s, 3H), 2.14 (s, 3H), 1.51 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.2 Hz, 3H). MS: m/z 356.2 (M+H+).

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-Bromo-1-fluoro-3-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; SMITH, Layton H.; PINKERTON, Anthony B.; HERSHBERGER, Paul; MALONEY, Patrick; MCANALLY, Danielle; (167 pag.)WO2019/32720; (2019); 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. 4117-09-3, name is 7-Bromo-1-heptene, A new synthetic method of this compound is introduced below., Product Details of 4117-09-3

Mg shavings (939 mg, 38.6 mmol) are suspended in Et2O (20 ml)and 1-bromohept-6-ene (3.385 g, 19.115 mmol) is added dropwise. Thereaction mixture is stirred at RT for 3 h. Then the Grignard reagent isadded to EtOSiCl3 (945 mg, 5.150 mmol), dissolved in Et2O (20 ml), at 0 C via cannula. The reaction mixture is allowed to warm to RT andthen stirred for 2 h. Subsequently, 20 ml of the solvent are removed invacuo and 20 ml of hexanes are added to precipitate the salts formedduring the Grignard reaction. The reaction mixture is ffiltered throughcelite and the solvent removed in vacuo. The crude product is purifiedby column chromatography (SiO2, hexanes : ethylacetate=8 : 1) and 2 from the first fraction. The colorless liquid 2d (510 mg, 0.778 mmol) isisolated from the second fraction as the major product in 30% yield. Tris(hept-6-enyl)ethoxysilane 21H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt,3Jtrans(1H-1H)=16.9, 3 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz,3H, H6), 4.99 (ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz, 3H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.3 Hz, 4J(1H-1H) =1.1 Hz, 3H, H7E), 3.65 (q, 3J(1H-1H)=6.9 Hz, 2H, H8), 2.00-2.07 (m, 6H, H5), 1.30-1.41 (m, 18H, overlappingH2, H3, H4), 1.17 (t, 3J(1H-1H) =6.9 Hz, 2H, H9), 0.56-0.61(m, 6H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X (ppm)=139.21(C6), 114.11 (C7), 58.37 (C8), 33.73 (C5*), 33.11 (C3*), 28.57 (C4),23.02 (C2), 18.65 (C9), 13.59 (C1), *assignments interchangeable; 29Si{1H} NMR (CDCl3, 79.4 MHz): X (ppm)=15.36 (s).Hexakis(hept-6-enyl)disiloxane 2d.1H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt, 3Jtrans(1H-1H)=16.9 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz, 6H, H6), 4.99(ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz,6H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.2 Hz, 4J(1H-1H) =1.2 Hz, 6H, H7E), 2.04 (dt, 3J(1H-1H) =6.7 Hz, 3J(1H-1H)=6.6 Hz, 12H, H5), 1.30-1.43 (m, 36H, overlapping H2, H3, H4), 0.56-0.61 (m, 12H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X(ppm)=139.16 (C6), 114.15 (C7), 33.69 (C5*), 33.01 (C3*), 28.57(C4), 22.91 (C2), 14.99 (C1), *assignments interchangeable

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:
Article; Guenther; Reibenspies; Bluemel; Molecular catalysis; vol. 479; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. category: bromides-buliding-blocks

Add 1,4-dibromo-2,5-difluorobenzene (1.09 g, 4 mmol), phenylboronic acid (1.21 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (468 mg, 0.4 mmol) THF (50 mL) and aqueous potassium carbonate (1M, 20 mL) were then evaporated and then th After cooling to room temperature, the layers were separated. The aqueous phase was extracted with dichloromethane (3¡Á50 mL). The residue was purified by silica gel column was using dichloromethane: hexane (1: 5) as eluent to give the product as a white solid (0.82g, 77.1%);

The synthetic route of 1,4-Dibromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Normal University; Ren Xiuhui; Zhu Fucheng; Zhang Xi; Geng Yan; (23 pag.)CN110003179; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-51-4, 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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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.

Example 14 3-Bromo-5-fluorobenzonitrile A 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3-dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity-filtered though Celite. The filtrate was rinsed three times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2*30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3*40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.10 g, 35%). 1H NMR (400 MHz, CDCl3) delta 7.62 (s, 1H), 7.54-7.50 (m, 1H), 7.35-7.32 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-2,2-difluorobenzodioxole

General procedure: Method A. A solution of Pd(OAc)2 (25.2 mg, 0.112 mmol) and triphenylphosphine (147 mg, 0.560 mmol) in absolute ethanol (4 mL) and anhydrous toluene (4 mL) was stirred at RT under nitrogen for 10 min. After that period, commercially available 5-chloro-2-nitrotoluene 4 (646 mg, 3.76 mmol), 4 mL of 2M aqueous Na2CO3, and the appropriate boronic acid R1B(OH)2 (6.03 mmol) were sequentially added. The resulting mixture was heated at 100 C in a sealed vial under nitrogen overnight. After being cooled to RT, the mixture was diluted with water and extracted with EtOAc. The combined organic phase were dried and concentrated. The crude product was purified by flash chromatography over silica gel column using n-Hex/EtOAc or CHCl3/MeOH mixtures as the eluent.

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 33070-32-5.

Reference:
Article; Granchi, Carlotta; Roy, Sarabindu; De Simone, Alessio; Salvetti, Irene; Tuccinardi, Tiziano; Martinelli, Adriano; MacChia, Marco; Lanza, Mario; Betti, Laura; Giannaccini, Gino; Lucacchini, Antonio; Giovannetti, Elisa; Sciarrillo, Rocco; Peters, Godefridus J.; Minutolo, Filippo; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5398 – 5407;,
Bromide – Wikipedia,
bromide – Wiktionary