Month: July 2021

Application of 51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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.

General procedure: 1-Bromo-4-methylbenzene (1.0 g, 5.88 mmol) was dissolved in 30 mL anhydrous THF under argon. The solution was cooled to -78 C before solution of n-BuLi (2.4 M) in hexane (3.4 mL, 8.16 mmol) was added dropwise. The reaction mixture was stirred for 10 min at -78 C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.9 g, 10.2 mmol) was added then. The reaction mixture was allowed to warm up to room temperature and stirred overnight before it was poured into ice water. The solution was extracted with 100 mL dichloromethane (CH2Cl2), the organic layer washed with 70 mL brine and dried with Na2SO4 before the solvent was removed. The crude product was purified by column chromatography on silica gel with petroleum ether/CH2Cl2 (10:1, v/v) as an eluent to give a white solid (1.1 g, 85% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-octylbenzene, its application will become more common.

Reference:
Article; Zhu, Minliang; Luo, Hao; Wang, Liping; Guo, Yunlong; Zhang, Weifeng; Liu, Yunqi; Yu, Gui; Dyes and Pigments; vol. 98; 1; (2013); p. 17 – 24;,
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Synthetic Route of 174508-31-7, These common heterocyclic compound, 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, 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 (2),4-pyridylboronic acid pinacol ester (2.01 g, 9.8 mmol),Tetrakis(triphenylphosphine)palladium (407 mg, 0.352 mmol),Potassium phosphate (5.95 g, 28 mmol) was added to a 250 mL flask.Add 70 mL of Compound 4 (1.08 g, 3.61 mmol) in a nitrogen atmosphere.1,4-dioxane solution,The reaction solution is heated to 90 C,Reaction 72h,After the reaction is completed, cool to room temperature.filter,The filter residue is washed with chloroform.The filtrate was spun in a rotary evaporator.After that, it was purified by silica gel column chromatography (eluent was a mixture of chloroform_methanol=200:1).Purification gives a yellow solid, compound 5,Yield 60%;

The synthetic route of 174508-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South University of Science and Technology of China; Su Fengyu; Wu Xiaowen; Tian Yanqing; Liu Yanjun; Luo Dan; Sun Xiaowei; (16 pag.)CN108997427; (2018); A;,
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Application of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Description 14:; 2-Bromo-3,6-difluorobenzaldehyde (D14)To solution of diisopropylamine (13.29 mL, 93 mmol) in THF (300 mL) at -78 0C, was added n-butyllithium (34.2 mL of 2.5M in hexanes, 85 mmol), dropwise over 10 mins. The mixture was stirred at -78 0C for 15 mins and then 2-bromo-1 ,4-difluorobenzene (15 g, 78 mmol) in THF (100 mL) was added dropwise over 15 mins maintaining the temperature below -65 C. After stirring for 1 hr at -78 0C, N,N-dimethylformamide (6.62 mL, 85 mmol) was added via syringe. The mixture was stirred at -78 0C for 30 mins and then quenched with sat. NH4CI solution and the mixture was allowed to reach room temperature. The product was extracted into ether and the extracts were dried (Na2SO4) and evaporated. Chromatography (silica, 0-100% dichloromethane in hexane) gave the title compound(D14) as a yellow solid (12.73 g)NMR (deltaH), (CDCI3): 7.16 (1 H, m), 7.35 (1 H, m), 10.32 (1 H, s).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1073-06-9, name is 1-Bromo-3-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 1073-06-9, Formula: C6H4BrF

Diacetoxypalladium (3.3 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (121 mg, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.61 mg, 0.03 mmol), 1-bromo-3-fluorobenzene (0.047 mL, 0.42 mmol) and cesium carbonate (165 mg, 0.51 mmol) suspended in 1,4-dioxane (3.3 mL). The resulting suspension was degassed with argon and then stirred at 100 C. for 20 h. The reaction mixture was allowed to cool to room temperature, and the crude product was purified by flash chromatography on silica gel eluting with 0 to 7% propanol in DCM. The solvent was evaporated to dryness to afford methyl 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (120 mg, 79%) as a yellow oil which solidified on standing. Mass Spectrum: m/z [M+H]+=453.

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-Bromo-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2012/264731; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Step 3) Synthesis of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethypplicnyl)-1H-imidazole 3-oxide (Compound 1-5) 1.0 g (4.1 mmol, 1.1 eq) of 1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide, 0.043 g (0.19 mmol, 5 mol %) of palladium acetate, 0.18 g (0.57 mol, 15 mol %) of tri(p-fluorophenyl)phosphine, 0.11 g (1.1 mmol, 30 mol %) of pivalic acid, and 1.0 g (7.4 mmol, 2.0 eq) of carbonic acid potassium were added to a reactor, followed by replacing the air with argon gas. 14 mol of anhydrous acetonitrile solution of 0.90 g (3.7 mmol, 1.0 eq) of 4-bromo-3-fluorobenzene trifluoride was added to the resulting mixture, followed by stirring over night at 70 C. The resulting reaction liquid was filtered over celite and concentrated under reduced pressure. The obtained crude crystal was washed with diethylether to obtain 1.1 g of the objective compound (yield: 73%). 1H-NMR of the obtained compound is shown below: 1H-NMR (400 MHz, CDCl3): delta 8.21(m, 1H), 7.80(m, 2H), 7.64(m, 111), 7.59(m, 2H), 7.57(m, 1H), 7.47(s, 1H), 3.57(d, 3H).

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-Bromo-2-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; AOYAMA, Hikaru; MATSUI, Maki; IWASA, Takao; FUJII, Kazushige; KOBAYASHI, Tomomi; SAKANISHI, Keita; (32 pag.)US2017/223958; (2017); A1;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, molecular formula is C7H6BrF3N2, 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. Recommanded Product: 113170-72-2

Na2S2O5 (1.64 g, 8.62 mmol) and 4-fluoro-benzaldehyde (891 mg, 7.18 mmol) were added to a sol. of 3-bromo-5-trifluoromethyl-l,2-diaminobenzene (1.65 g, 6.47 mmol) – -in DMA (40 ml). The r.m. was stirred overnight at 70 0C. Then, the r.m. was cooled to r.t. and poured into water. The solid was filtered off, washed with water, and suspended in DIPE and some drops of 2-propanol. The resulting solid was filtered off, washed with DIPE, and dried. Yield: 1.95 g of intermediate 64 (84 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113170-72-2, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
Bromide – Wikipedia,
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Application of 586-61-8, A common heterocyclic compound, 586-61-8, name is 1-Bromo-4-isopropylbenzene, molecular formula is C9H11Br, 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.

A suspension of 128.8 g (0.8 mol) of 1H-indole-2-carboxylic acid, of 159.2 g (0.8 mol) of 4-bromocumene, of 111.6 g (0.808 mol) of potassium carbonate and of 8 g (0.1 mol) of copper oxide in 200 ml of dimethylformamide is stirred at reflux for 24 hours. After cooling, 6 l of water are added to the beige suspension obtained. The suspension is filtered and then the insoluble material is taken up in 1 l of a 5N hydrochloric acid solution. This mixture is extracted with 500 ml of dichloromethane. The organic phase is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. After drying under reduced pressure, 204.4 g of a white solid are obtained, which solid is used as is in the following stage. Melting point=203-204 C.

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; SANOFI-AVENTIS; US2007/149602; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, molecular formula is C5H9Br, 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. Safety of (Bromomethyl)cyclobutane

A stirred solution of ketimine 10.01 (50 g, 187.1 mmol) under N2 in dry THF (400 mL) was cooled to-78 C and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv. ) in THF. The reaction mixture was warmed to 0 C and stirred for 1 h and treated with bromomethyl cyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et20 (300 mL) and treated with aq. HCI (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et20 (1 L). The aqueous layer was made basic to pH-12-14 with NaOH (50 % aq. ) and extracted with CH2CI2 (3×300 mL). The combined organic layers were dried (MgS04), filtered, and concentrated to give the pure amine (10.02, 18 g) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17247-58-4, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2005/85197; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 34950-82-8, 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. 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

10.2 N-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-5-fluoro-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxamide (Compound 9) 0.4 g (1.4 mmol) of the amide prepared in the preceding step, 0.31 g (1.47 mmol) of 7-bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, 0.08 g (0.42 mmol) of copper iodide, 0.39 g (2.79 mmol) of potassium carbonate and 10 mL of dry dioxane are introduced into a pressure tube equipped with a magnetic stirrer. The suspension is degassed, 53 mg (0.46 mmol) of trans-1,2-cyclohexanediamine are added, and the tube is heated at 120 C. with stirring for 16 hours. After this time, 50 mL of ethyl acetate and 50 mL of water are added to the medium. The aqueous phase is separated out and then extracted with 2*30 mL of ethyl acetate. The organic phases are combined, washed with 50 mL of water, dried over sodium sulfate and then concentrated under reduced pressure. The resulting product is purified by chromatography on a column of silica, eluding with a mixture of heptane and ethyl acetate, followed by crystallization from a mixture of heptane and dichloromethane. 0.4 g of the expected product is thus isolated. m.p.: 265-266 C. 1H NMR (DMSO D6), delta (ppm): 10.22 (s, 1H); 7.98 (s, 1H); 7.58 (m, 2H); 7.34 (m, 3H); 7.18 (m, 1H); 7.06 (m, 1H); 6.91 (m, 2H); 6.58 (s, 1H); 5.9 (s, 2H); 4.14 (m, 2H); 3.4 (m, 2H).

The synthetic route of 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2011/9400; (2011); 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. 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H3BrF4

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were placed benzoyl chloride (5a, 0.17 mL, 1.5 mmol), Cu2O (0.027 g, 0.18 mmol), 2,2′-bipyridyl (0.019 g, 0.12 mmol), and a DMF solution of 2-Zn (0.61 M, 1.0 mL, 0.61 mmol), and the whole were stirred at room temperature for 20 h. The resultant was poured into water and the organic products were extracted with Et2O three times. The combined organic layers were dried over anhydrous Na2SO4, then filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the corresponding 6a (0.13 g, 0.56 mmol) in 92% yield as a colorless oil.

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 18599-22-9.

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