Tag: M.W=200-300

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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

To a round bottom flask was added 4-bromo-N2-methylbenzene-1,2-diamine (1-2) (9.07 g, 45.1 mmol), sulfamide (8.84 g, 92 mmol), and finally anhydrous pyridine (75 mL). The reaction mixture was then heated to 125C while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 14 hours. The crude reaction mixture was then allowed to cool to room temperature, suspended in ethyl acetate and added 6N HCl until pH <3. Crude mixture was then filtered. Filtrate organics were separated, then washed with 6N HCl twice dried over sodium sulfate, filtered, and concentrated to give 6- bromo-1 -methyl- 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3). HRMS (M+H)+:observed = 262.9486, calculated = 262.9484. The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
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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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-3-(tert-butyl)benzene

A 1.7 M solution of tert-butyllithium in pentane (2.60 mL, 4.42 mmol) was added to a solution of 1-bromo-3-tert-butyl-benzene (426 mg, 2.00 mmol) in tetrahydrofuran (5 mL) at-78 ¡ãC. After stirring for 1 h, tributyltin chloride (0.57 mL, 2.10 mmol) was added at-78 ¡ãC. After stirring for 18 h, during which time the solution warmed to ambient temperature, the solution was diluted with water and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 976 mg (115percent yield) of tributyl- (3-tert-butyl-phenyl)-stannane as a impure light yellow oil.

According to the analysis of related databases, 3972-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); A1;,
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Synthetic Route of 24358-62-1, 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 24358-62-1 as follows.

tert-Butyl 1-(4-bromophenyl)ethylcarbamate 1-(4-Bromophenyl)ethanamine (3.58 ml, 25 mmol) and Et3N (4.39 ml, 31.25 mmol) was dissolved in CH2Cl2 and cooled to 0 C. To this was added (Boc)2O (6.0 g, 27.5 mmol) and the resulting solution was stirred 5 minutes at 0 C. for 5 and then 3 h at room temperature. The reaction was washed with HCl (50 ml, 1M) followed by NaHCO3 (sat) (2*50 ml). The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by precipitation from MeOH/H2O (10:1) to give 6.35 g (85%) of the title compound as a white powder. 1H NMR (CDCl3) delta 7.45 (d, 2H), 7.18 (d, 2H), 4.83-4.70 (br, 2H), 1.46-1.32 (br, 12H).

According to the analysis of related databases, 24358-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RESPIRATORIUS AB; US2012/40942; (2012); A1;,
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Reference of 80058-84-0, A common heterocyclic compound, 80058-84-0, name is 4-Bromo-2,6-diisopropylaniline, molecular formula is C12H18BrN, 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.

With stirring, 21 g (0.15 mol) of potassium carbonate are initially added to 141 g (1.5 mol) of phenol in 500 g of toluene, followed by the addition of 168 g (1.5 mol) of a 50percent aqueous solution of potassium hydroxide. The entire water of reaction is then separated under reflux, and then ca. 400 g of toluene are removed by distillation. The residue is dissolved in 700 g of dimethyl formamide. After addition of 6 g (0.05 mol) of copper carbonate, solvent is distilled off until the temperature of the reaction mixture is 140¡ã C. Then 256 g (1 mol) of 4-bromo-2,6-diisopropylaniline are added at 140¡ã C. and the mixture is kept for 10 hours at 140¡ã C. The dimethyl formamide is then removed by vacuum distillation, the residue is extracted with water, and the product is taken up in toluene. After stripping off the toluene, the crude product is purified by vacuum distillation, giving 215 g (80percent of theory) of 4-phenoxy-2,6-diisopropylaniline with a boiling point of 142¡ã-145¡ã C./0.04 mbar and a melting point of 69¡ã-71¡ã C., in the form of a bright red product.

The synthetic route of 80058-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4997967; (1991); A;,
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Application of 402-43-7, 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. 402-43-7, name is 1-Bromo-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an undivided cellequipped with a Zn sacrificial anode (1.5 x 1.0 cm2) and a Pt cathode (1.5 x 1.0 cm2) was placed a DMF(3 mL) solution of 4-bromopropiophenone (4a, 0.053 g, 0.25 mmol), 1 (0.14 g, 7.6 x 10-2 mmol),[Bu4N+][Tf2N-] (0.16 g, 0.30 mmol), and a catalytic amount of PdCl2(PPh3)2 (0.0086 g, 1.2 x 10-2 mmol).The solution was electrolyzed under constant current conditions (10 mA) at 60 C until 2 F/mol-4a ofelectricity was passed. The reaction mixture was poured into 5% aq. HCl (12 mL). The mixture wasextracted with AcOEt (10 mL x 3). The combined organic layer was washed successively with waterand brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified bycolumn chromatography (SiO2, toluene/AcOEt = 10/1) to afford 4,4?-dipropanoylbiphenyl (5a, 0.030 g,0.11 mmol, 89%).

The synthetic route of 1-Bromo-4-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kuroboshi, Manabu; Kojima, Atsuki; Tanaka, Hideo; Heterocycles; vol. 94; 11; (2017); p. 2132 – 2140;,
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Related Products of 393-37-3, A common heterocyclic compound, 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride, molecular formula is C7H3BrF4, 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.

4-bromo-1-fluoro-2-(trifluoromethyl)benzene (2.00 g, 8.2 mmol) was placed in a 250 ml reaction flask, followed by injecting and evacuating nitrogen gas three times. Next, dehydrated THF (50 ml) was added into the reaction flask, followed by slowly adding 3.62 ml n-butyllithium in hexane solution (9.1 mmol) (2.5M, 9.1 mmol) at -78 C. and stirring at the same temperature for 30 minutes. Thereafter, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.85 ml, 9.1 mmol) was added into the reaction flask to obtain a mixture, and the temperature of the mixture was raised to room temperature, followed by stirring at room temperature for 12 hours. Next, water was added to terminate the reaction followed by removing THF using a rotary evaporator. Then, dichloromethane and water were added into the mixture for extraction. The dichloromethane layer was collected and added with magnesium sulfate to remove water therein. After water was removed, the dichloromethane layer was filtrated and the filtrate was collected. Next, the dichloromethane layer was concentrated by means of reduced pressure distillation to obtain a colorless oily liquid (1.95 g, 6.7 mmol, 82% yield).The spectrum analysis for the colorless oily liquid is: 1H NMR (400 MHz, CDCl3, 298K), delta(ppm): 8.03 (d, JHF=7.6 Hz, 1H), 7.98?7.90 (m, 1H), 7.16 (t, JHH=9.2 Hz, 1H), 1.35 (s, 12H).

The synthetic route of 393-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chi, Yun; Hsu, Chien-Wei; Ho, Shu-Te; US2013/18189; (2013); A1;,
Bromide – Wikipedia,
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Electric Literature of 130723-13-6, 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. 130723-13-6 name is 1-Bromo-3-fluoro-5-(trifluoromethyl)benzene, 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.

The 4-hydroxy-4-[3-(naphth-2-ylthio)-5-trifluoromethylphenyl]tetrahydropyran used as a starting material was obtained as follows:- Sodium hydride (60% w/w dispersion in mineral oil; 0.5 g) was added portionwise to a mixture of 2-naphthalenethiol (1.42 g) and DMA (30 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of 1-bromo-3-fluoro-5-trifluoromethylbenzene (2.43 g) in DMA (10 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography using hexane as eluent. There was thus obtained 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide (1.37 g, 40%), as an oil. A solution of the product so obtained in THF (10 ml) was cooled to -60C and n-butyl-lithium (1.6 M in hexane; 2.3 ml) was added dropwise.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-fluoro-5-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; ICI PHARMA; EP409413; (1991); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, 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 393-36-2, Safety of 4-Bromo-3-(trifluoromethyl)aniline

(ii) 4-Cyano-3-(trifluoromethyl)aniline was prepared by the method of L. Friedman and H. Shechter (J. Org. Chem. 26, 2522, 1961)): A mixture of 5-amino-2-bromobenzotrifluoride (12.00 g, 50 mmol), CuCN (5.37 g, 60 mmol), and DMF (7.5 mL) was heated under reflux for 2 h. It was poured into 30% w/v NaCNaq (150 mL) and extracted with ether (75 mL). The ether layer was washed sequentially with 10% NaCNaq (100 mL), H2O (100 mL), and brine (100 mL), dried (Na2SO4) and evaporated to dryness to give the crude product (8.00 g). This was flash chromatographed on silica (700 g) using 20% ether in CH2Cl2 as the eluant to give the pure product as a light tan solid (7.03 g, 76%) suitable for further use. An analytical sample recrystallized from EtOH/H2O as off-white needles, mp 142-143C, NMR satisfactory, Anal. (C8H5F3N2) C,H,N,F.

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, 4-Bromo-3-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; EP365763; (1990); A1;,
Bromide – Wikipedia,
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Synthetic Route of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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 1; Preparation of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I2000 g of 3-bromo-5-trifluoromethylaniline of formula II, 1368 g of 4-methylimidazole of formula III, 181 g of 8-hydroxyquinoline, 238 g of CuI, 666.6 g of NaOH, 933 g of CaO and 7000 ml of DMSO were loaded into a 10 L of 3-neck flask. The reaction mixture was protected with nitrogen and was then stirred at 120 C. for 69 hours while monitoring for the consumption of 3-bromo-5-trifluoromethyaniline by HPLC. Heating was stopped when 3-bromo-5- trifluoromethyaniline/4-methylimidazole is not more than 5%. The reaction mixture was cooled down to 45-50 C. and poured into a 50 L reactor. 8.4 L of 14% ammonia was added dropwise and then stirred for 1 hour at 45-50 C. The mixture was cooled down to room temperature. 16.8 L of water and 10 L of ethyl acetate were added to the extract. The upper organic layer was separated and filtered through the filter aid. The lower aqueous layer was washed with 7.5L of ethyl acetate and combined with the above filtrate. The combined organic layer was washed with 5 L¡Á3 of 5% of brine for three times. The upper organic layer was separated and dried over 1 kg of anhydrous Na2SO4 overnight. The mixture was filtered and concentrated to obtain 2.3 kg of solid. The residue was dissolved in 2 L of ethyl acetate at 45 C. To the solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 0-15 C. and stirred for 1 hour. A large amount of precipitate was formed and filtered. The filtered cake was dissolved in 2 L of ethyl acetate at 45 C. The solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 15-0 C. and stirred for 1 hour. A large precipitate was formed and filtered. The filter cake was dried at 45 C. and 954 g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I were obtained. (Yield: 47.5%). The obtained compound of formula I had purity of 99.7% on area by HPLC and contained 0.13% on area by HPLC, of the 5 methyl isomer impurity.

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-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2862-39-7, 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 2862-39-7 as follows.

A solution of 5-(2-hydroxyphenyl)-9-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]-3,9- diazaspiro[5.5]undecan-2-one (stereoisomer 1) (50.0 mg, 105 pmol) (Example 175) and caesium carbonate (68.4 mg, 210 pmol) in DMF (1 ml_) was was stirred for 10 min at room temperature. Then 2-bromo-N,N-dimethylethan-1 -amine hydrogen bromide (1/1) (24.4 mg, 105 pmol) was added. The mixture was stirred at 80 for 12 hours. The reaction mixture was concentrated in vacuo. The residue was purified via preparative HPLC (method 6) to give the title compound 15.3 mg (95 % purity, 25 % yield).LC-MS (Method 2): Rt= 1.20 min; MS (ESIpos): m/z = 548 [M+H]+Optical rotation (method OR1): +71.1?(methanol).1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.390 (0.18), 0.421 (0.34), 0.444 (0.20), 0.763 (0.46), 0.797 (0.44), 0.851 (0.16), 0.894 (0.24), 0.917 (0.40), 0.927 (0.40), 0.950 (0.26), 1.107(1.85), 1.163 (0.62), 1.232 (0.84), 1.269 (0.32), 1.481 (0.62), 1.515 (0.50), 1.899 (0.42), 1.942(0.52), 2.003 (0.64), 2.046 (0.68), 2.121 (0.54), 2.170 (11.10), 2.191 (0.44), 2.225 (16.00), 2.284 (0.58), 2.518 (5.23), 2.522 (3.58), 2.544 (0.50), 2.556 (0.64), 2.570 (0.50), 2.586 (0.54),2.602 (1.49), 2.615 (0.94), 2.629 (1.11), 2.664 (1.15), 2.668 (1.31), 2.673 (1.01), 2.841 (0.30), 2.869 (0.54), 2.908 (0.36), 2.945 (0.58), 2.954 (0.48), 2.967 (0.46), 3.096 (0.30), 3.130 (0.46),3.163 (0.26), 3.244 (0.50), 3.273 (1.15), 3.289 (2.55), 3.367 (0.36), 3.398 (0.24), 3.419 (0.52),3.431 (0.58), 3.446 (0.42), 3.459 (0.36), 3.494 (0.32), 3.513 (0.52), 3.527 (0.60), 3.566 (5.03),3.966 (0.32), 3.976 (0.66), 3.991 (1.39), 4.006 (1 .39), 4.021 (0.72), 4.034 (0.48), 4.050 (0.34), 4.063 (0.18), 4.102 (0.38), 4.135 (0.58), 4.167 (0.24), 4.191 (0.18), 6.716 (0.66), 6.734 (0.76),6.894 (0.30), 6.912 (0.58), 6.931 (0.34), 6.965 (0.54), 6.984 (0.96), 7.004 (1 .75), 7.026 (1 .51 ),7.172 (1 .35), 7.191 (1 .85), 7.219 (1.00), 7.237 (0.76), 7.267 (0.58), 7.285 (1 .93), 7.304 (2.15),7.324 (1 .00), 7.340 (0.66), 7.350 (0.80), 7.358 (0.78), 7.434 (1.97), 7.441 (1 .63), 7.451 (1 .13),7.477 (0.60), 7.495 (0.90), 7.514 (0.40), 7.549 (0.98), 7.554 (1.00), 7.629 (0.66).

According to the analysis of related databases, 2862-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; BUCHGRABER, Philipp; AIGUABELLA FONT, Nuria; WITTROCK, Sven; HEINRICH, Tobias; BRAeUER, Nico; KUHNKE, Lara, Patricia; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; KOPITZ, Charlotte, Christine; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; (754 pag.)WO2020/48831; (2020); A1;,
Bromide – Wikipedia,
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