Month: July 2021

Electric Literature of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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.

Freshly crystalized BS (13.84 g, 77.80 mmol, 1.2 eq) was added to the solution of 1- bromo-4-methylnaphthalene (15.0 g, 67.84 mmol, 1.0 eq) and AIBN (1.11 g, 6.78 mmol, 0.1 eq) in carbon tetrachloride (150 mL) and the mixture was stirred at 80 C for 16 h under nitrogen atmosphere. After complete consumption of starting material, water was added to the reaction mixture and extracted with DCM. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulfate, filtered, and the solvent evaporated from the filtrated under reduced pressure to obtain l-bromo-4-(bromomethyl)naphthalene. LCMS: Purity 96.83%

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-methylnaphthalene, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 7073-94-1, 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. 7073-94-1, name is 1-Bromo-2-isopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether-ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC-MS analysis). The purity of the recovered MeOH was measured as more than 99 % by GC, and the water content of the recovered MeOH was measured as less than 0.12 % by use of the Karl Fischer method.

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-isopropylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Ying; Ji, Si-Zhe; Chen, Cheng; Liu, Hong-Wei; Zhao, Jian-Hong; Zheng, Yu-Lin; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 41; 11; (2015); p. 8651 – 8664;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)aniline

N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline 600 mg (2.50 mmol: 1.00 eq) of 3-ammo-5-bromo-1-trifluoromethylbenzene, then 1028 mg (12.50 mmol; 5.00 eq) of formaldehyde and finally 4 g of acetonitrile were introduced into a 50 ml round-bottomed flask. The reaction mixture was brought to 30 C. It was left for 30 min,then 314.21 mg (5.00 mmol; 2.00 eq) of sodium cyanoborohydride were added, followed, one minute later, by 900 mul of acetic acid; a strong effervescence was noted. The reaction medium was stirred at 35 C. for 3 h. Next, the initial pH of 10.9 was brought back to 7.9 by adding 1 N hydrochloric acid. ;The medium was evaporated under vacuum and then extracted four times with ether. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by Hash chromatography on silica (Merck column of 30 g of SiO2 15-40 mum) with a 100% toluene eluent (liquid deposit in the eluent). The fractions containing the targeted product were combined and then evaporated under reduced pressure to give 481 mg of 3-dimethylamino-5-bromo-1-trifluoromethylbenzene in the form of a colorless liquid. Yld: 72%. 1H NMR (300 MHz, CHCl3-d) deltappm 2.98 (s, 6H) 6.78 (s, 1H) 6.93 (s, 1H) 7.04 (s, 1H).

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 54962-75-3.

Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

EXAMPLE 4 2-(2-amino-4-fluorophenyl)-3-methyl-2-cyclopenten-1-one 4.937 g (25.982 mmol) of 2-bromo-4-fluoroaniline, 4.00 g (28.584 mmol) of 5-methyl-1-cyclopenten-2-one boronic acid compound, 0.30 g (0.260 mmol) of tetrakis(triphenylphosphine)palladium, and 4.13 g (38.978 mmol) of sodium carbonate were loaded to 250 mL schlenk flask, and then 80 mL of degassing DME and 27 mL of H2O that had been purged with N2 were added thereto using a syringe. The mixture was reacted at 90° C. for 12 hours. The work-up was the same as in Example 3 (3.84 g, 72percent). 1H NMR (CDCl3): =6.83 (t, J=7.6 Hz, 1H, Ph), 6.48 (t, J=7.6 Hz, 1H, Ph), 6.43 (d, J=10.4 Hz, 1H, Ph), 3.82 (br s, 2H, NH2), 2.73-2.71 (m, 2H, CH2CP), 2.58-2.55 (m, 2H, CH2Cp), 2.09 (s, 3H, CH3); 13C {1H} NMR (CDCl3): =207.93, 175.26, 168.18(d, J=242.6 Hz, PhC-F) 146.47(d, J=5.7 Hz, Ph), 138.76, 131.90(d, J=9.8 Hz, Ph), 113.71, 105.08(d, 22 Hz, Ph), 102.91 (d, 22 Hz, Ph), 34.79, 32.22, 18.63

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; LG Chem, Ltd.; US7538239; (2009); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 24358-62-1, A common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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.

First, N-(1-(4-(2,5-bicyclo[2.2.1]heptenyl) phenyl)ethyl)maleimide was synthesized in three stages. 1-(4-Bromophenyl)ethylamine (25.1 g, 0.125 mol) was dissolved in diethyl ether (100 mL), and slowly added dropwise at 0 C. to a diethyl ether solution (200 mL) of maleic anhydride (10.4 g, 0.106 mol). The reaction solution was stirred for two hours at room temperature, and the solid that precipitated was filtered out and washed several times by diethyl ether. The solid filtered out and sodium acetate (1.20 g) were dissolved in acetic anhydride (120 mL), and stirred for four hours at 140 C. The solvent was distilled off under reduced pressure, water was added, and the solution was extracted by methylene chloride. The organic layer was dried using anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using chloroform-hexane mixed solvent (mixture ratio 4:1) as the developing solvent, and N-(1-(4-bromophenyl)ethyl)maleimide (23.5 g, 84.0 mmol, 79%) was obtained as a white solid. The spectra data of N-(1-(4-bromophenyl)ethyl)maleimide were as follows. 1H NMR (400 MHz, CDCl3): delta 7.46-7.43 (m, 2H), 7.31-7.28 (m, 2H), 6.64 (s, 2H), 5.30 (q, J=7.6 Hz, 1H), 1.79 (d, J=7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3): delta 170.3, 139.1, 140.0, 131.5, 129.0, 121.6, 48.9, 17.4; HRMS (APCI, positive): [M+] calcd. for C12H10BrNO2, 278.9895; found 278.9904.

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Science and Technology Agency; Yabu, Hiroshi; Saito, Yuta; Saito, Shohei; Yamaguchi, Shigehiro; Nobusue, Shunpei; (47 pag.)US10442886; (2019); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 61326-44-1, 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. 61326-44-1 name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, 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.

In a polar solvent, 1,1,2,2-tetrakis (4-bromophenyl) ethylene, 1,1,2,2-tetrakis (4-bromophenyl)1H-1,2,4-triazole,Potassium carbonate andCopper oxide in the reaction conditions;Wherein 1,1,2,2-tetrakis (4-bromophenyl) ethylene:1H-1,2,4-triazole:Potassium carbonate:The molar ratio of copper oxide is 2: 10-15: 30: 1;The reaction temperature is 80-200 DEG C, the reaction time is 12-120 hoursThe present invention is preferably 1,1,2,2-tetrakis (4-bromophenyl) ethylene:1H-1,2,4-triazole:Potassium carbonate:The molar ratio of copper oxide was2: 10-15: 30: 1;Reaction temperature 100 ,The reaction time was 48 hours.In a polar solvent,Using the “one-pot method”1, 1, 2,(4-bromophenyl) ethene, 1H-1,2,4-triazole, potassium carbonate and copper oxide were heated under heating to produce 1,1,2,2-tetrakis [4-(1H-1,2,4-triazol-1-yl) phenyl] ethylene (L). Yield 60percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,2,2-Tetrakis(4-bromophenyl)ethene, and friends who are interested can also refer to it.

Reference:
Patent; Tianjin Normal University; Wang, Ying; (11 pag.)CN105524086; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2, The chemical industry reduces the impact on the environment during synthesis 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, I believe this compound will play a more active role in future production and life.

Synthesis of intermediate 4-(biphenyl-4-yl)-1-(3-bromo-5-tert-butylphenyl)-1H-imidazole 13 4-(Biphenyl-4-yl)-1H-imidazole 12 (3773 mg, 17.13 mmol, 1.0 eq), CuI (326 mg, 1.71 mmol, 0.1 eq), L-proline (394 mg, 3.42 mmol, 0.2 eq), 1,3-dibromo-5-(1,1-dimethylethyl)-benzene (8.00 g, 27.40 mmol, 1.6 eq) and K2CO3 (4735 mg, 34.26 mmol, 2.0 eq) were added to a dry pressure tube equipped with a magnetic stir bar. The vissel was then evacuated and backfilled with nitrogen, this evacuation and backfill procedure was repeated for a total of three times. Then DMSO (35 mL) were added in a nitrogen filled glove box. The mixture was bubbled with nitrogen for 5 minutes. The tube was sealed before being taken out of the glove box. The mixture was stirred in an oil bath at a temperature of 105-115 C. for 3 days. Then the mixture was cooled to ambient temperature, filtered and washed with a plenty of ethyl acetate. The filtrate was washed with water three times, dried over sodium sulfate, filtered, concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1-3:1) as eluent to obtain the desired product 13 as a brown-red solid 2.023 g in 26% total yield for the two steps. 1H NMR (DMSO-d6, 400 MHz): delta 1.37 (s, 9H), 7.38 (t, J=7.2 Hz, 1H), 7.49 (t, J=8.0 Hz, 2H), 7.55 (d, J=1.6 Hz, 1H), 7.32-7.75 (m, 5H), 7.88 (d, J=1.2 Hz, 1H), 7.98 (d, J=8.4 Hz, 2H), 8.49 (s, 2H).

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, 1,3-Dibromo-5-(tert-butyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Li, Jian; Li, Guijie; US2015/194616; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 626-88-0, name is 1-Bromo-4-methylpentane, 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 626-88-0, Recommanded Product: 626-88-0

To a solution of 7-(3,4-dimethoxybenzyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2- amine (227 mg, 0.71 mmol, 1.00 equiv) in DMF (50 mL) was added l-bromo-4- methylpentane (141 mg, 0.85 mmol) and then NaH (34 mg, 1.42 mmol). The resulting solution was stirred for 4 hours at room temperature. The reaction was then quenched by the adding 50 mL of H2O/ice. The resulting solution was extracted with 3 x 50 mL of EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated under vacuum using a rotary evaporator. The residue was purified by recrystallization from EA : hexane (1 : 5), resulted in 39 mg (14%) of 7-(3,4-dimethoxybenzyl)-4-chloro-5-(4-methylpentyi)-5H- pyrrolo[3,2-d]pyrimidin-2-amine as a yellow solid. 1H NMR (300 MHz, CDCl3) delta 0.86 (6H, s), 1.15 (2H, m), 1.61 (IH, m), 1.75 (2H, m), 3.85 (6H, s), 3.95 (2H, s), 4.19 (2H, s), 4.87 (2H, s), 6.80-6.89 (4H, m). MS m/z: 403 [M+l] + .

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-4-methylpentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 626-39-1, These common heterocyclic compound, 626-39-1, name is 1,3,5-Tribromobenzene, 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.

[0372] 1,3,5-Tribromo-benzene (31.4 g, 100 mmol) was dissolved under argon in a flame dried three-neck flask in 1000 mL diethylether and the solution was cooled to -72C. A solution of 62 mL r°BuLi (1.6 M in hexane, 100 mmol) was added to the resulting suspension in such a fashion that temperature did not rise above -7O0C. The mixture was stirred for 30 min at -750C and the reaction was monitored by HPLC. A solution of 10.4 g (100 mmol) 3-cyanopyridine in 100 mL diethylether was added in such a fashion that temperature did not rise above -710C. The mixture was stirred at -75C for 60 min and the reaction was monitored by HPLC. The cooling bath was removed and warmed to -250C. 2 N HCl (250 mL) was added and the mixture was stirred for 20 min at room temperature. The mixture was made alkaline by addition of 1 N NaOH. The product was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4. The product was purified by chromatography (700 g silica agel, CH2Cl2, then CH2Cl2 / ethyl acetate 1:1, UV) to yield 27.7 g (81 %) of (3,5-dibromo-rhohenyl)-pyridin-3-yl-methanone.

The synthetic route of 626-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 327-51-5, 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.

Example i-7: methyl 5-fluoro-2-methoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxa borolan-2-yl)benzoate (i-7)Scheme i-7.i-7 i) Preparation of 4-bromo-2,5-difluorobenzoic acid (i-7b)To a solution of l,4-dibromo-2,5-difluorobenzene (i-7a) (1.1 g , 4 mmol) in Et20 (10 mL) at – 78 C was added n-BuLi (2.5M in hexane, 1.6 mL, 4 mmol) dropwise. The mixture was stirred for 30 min at -78 C and then quenched with an excess of freshly crushed dry ice. After 15 min, the mixture was brought to rt and diluted with H20. The aqueous layer was separated, and the organic layer was extracted with 10% aq. Na2C03. The combined aqueous layers were acidified with 1M HC1 and extracted with EtOAc. The combined organic layers were dried with Na2S04 and concentrated to give the title compound. LCMS (ESI) calc’d for C7H3BrF202 [M+H]+: 237, found: 237

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; N.V. ORGANON; KARSTENS, Willem Frederik Johan; STELT, Mario van der; CALS, Jos; AZEVEDO, Rita Corte Real Goncalves; BARR, Kenneth Jay; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; DUAN, Xiaobang; WO2012/106995; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary