Tag: M.W=100-200

Application of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

20 g (109 mmol) 2-(4-Bromophenyl)-cyclobutyl was dissolved in 150 ml dry THF and cooled to -78 C. 44 ml (109 mmol, 2.5 M solution) of n-Buli was added dropwise and the solution was stirred for one hour at -78 C. 2′- Bromo-biphenyl-2-carboxylic acid (43.6 mmol, 12.7 g) was dissolved in 25 ml THF and added to the n-BuLi solution at -78 C. The reaction mixture was stirred for 1 h at -78 C and then warmed to RT over the weekend. (0187) Ammoniumchloride solution was added to quench the reaction and the mixture was extracted with ethyl acetate. The combined organic phases were dried and the solvent was evaporated in vacuo. The resulting crude product was dissolved in 60 ml dry Toluene and 60 ml Hydrochloric acid (37%) as well as 1 15 ml acetic acid was added. The reaction was stirred at 80 C over night. After cooling down to RT the water was added, the aqueous phase was extracted with toluene and the combined organic phases were washed with water and dried with Na2SO4. The solvent was removed in vacuo. The resulting solid was recrystallized in (0188) Heptane/Toluene. 16 was obtained as a white product with 85% yield (0189) (37.1 mmol, 16.6 g). (0190) 5 I6 (15 g, 33.4 mmol), o-biphenylamine (6.2 g, 36.7 mmol) and Sodium-f- butylate (10.6 g, 1 10 mmol) were dissolved in 200 ml toluene. The mixture was degassed for 15 minutes and subsequently Pd(dppf)CI2 (1 .8 g, 2.2 (0191) mmol) was added. The solution was heated at reflux for 4 hours and then (0192) ^ Q cooled to RT. The mixture was filtered over Alox using toluene as the (0193) solvent. The resulting solid was recrystallized from toluene/heptanes. I7 was obtained as a white solid with a yield of 63% (1 1 .3 g, 21 mmol). (0194) 4.7 g (8.5 mmol) 2,7-dibromo-9,9-dioctyl-fluorene and 10 g (18.6 mmol, 2.2 1 eq) 17 were added to 100 ml Toluene. Subsequently 1 .5 g (1 .7 mmol, 0.2 (0195) eq) Pd2dba3 and 1 .6 g (17 mmol, 2 eq) Sodium-f-butylate were added and the mixture was degassed with argon. After 5 min degassing 3.8 g (1 .7 (0196) mmol, 0.2 eq) tri-f-butylphosphine was added and the reaction was stirred at reflux over the weekend. After cooling to RT the mixture was filtered over (0197) 20 (0198) Celite and subsequently purified via Soxhlet using Toluene as the solvent. (0199) The resulting solid was purified via flash chromatography. 9.7 g (6.6 mmol, 78%) of P8 was obtained.

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; SCHEIBLE, Katja Maria; ECKES, Fabrice; HEIL, Holger; BURKHART, Beate; JOOSTEN, Dominik; MONTENEGRO, Elvira; (93 pag.)WO2018/65357; (2018); A1;,
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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 17247-58-4 as follows. Recommanded Product: (Bromomethyl)cyclobutane

4e. Preparation of Cyclobutylcarbinylsulfonamide A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7 g (91 mmol) of sodium iodide in 150 mL of acetone was heated to reflux overnight and then cooled to room temperature. The inorganic solids were removed by filtration and the acetone and cyclopropylcarbinyl iodide (8.41 g, 46%) were removed by distillation (ambient temperature and 150 torr at 80 C., respectively). A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30 mL of anhydrous diethyl ether cooled to -78 C. was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyllithium in cyclohexanes and the solution was stirred for 5 minutes. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110 mL of hexanes cooled to -78 C., the mixture warmed to room temperature over 1 hour and was then carefully concentrated in vacuo. This mixture was redissolved in diethyl ether, washed once with some ice-cold water, dried (MgSO4), filtered, and concentrated carefully. This mixture was redissolved in 30 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnight. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount of dichloromethane in hexanes with 1-2 drops of methanol to provide 1.39 g (42%) of the desired product as a white solid. 1H NMR (CDCl3) delta 1.81-2.03 (m, 4H), 2.14-2.28 (m, 2H), 2.81-2.92 (m, 1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 13C NMR (CDCl3) delta 19.10, 28.21, 30.64, 60.93. MS m/e 148 (M-H)-.

According to the analysis of related databases, 17247-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
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Electric Literature of 1003-99-2, 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.

To a solution of 2-bromo-5-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at O0C under N2 atmosphere was added dropwise IM NaHMDS (2.5 eq.) The reaction was stirred for 15 minutes at 00C, and a solution of di-tert -butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH.(R). system (ISCO) using 0-5percent ethyl acetate in hexane to give the product as light yellow oil.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
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Application of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

To a suitable amount of a solvent (a mixture of 1,4-dioxane and polyethylene glycol 200 (PEG-200) in a volume ratio of 1: 2.5) was added 100 mmol of the compound of the above formula (I) (II), 6 mmol of a two-component catalyst (1.2 mmol of 1,5-cyclooctadiene (acetoacetate) iridium and 4.8 mmol of bis (tricyclohexylphosphine) nickel chloride (NiCl2(PCy3)2Proline t-butyl ester hydrochloride and 200 mmol NaHS (in the form of a 35% by mass aqueous solution), and then the temperature was raised to 90 C with stirring, and the mixture was stirred at room temperature for 10 minutes. The reaction was stirred at this temperature for 8 hours;After the completion of the reaction, the reaction solution was cooled to room temperature, filtered, and the pH of the filtrate was adjusted to neutral. The extract was shaken with n-hexane for 2-3 times. The organic phase was combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The mixture was eluted with a 2: 1 by volume mixture of chloroform and acetone. The eluate was collected, and the solvent was distilled off under reduced pressure to give the compound of the formula (III) in a yield of 97.4%.

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

Reference:
Patent; Wang, Jianjun; Li, Guiyan; (9 pag.)CN106083729; (2016); A;,
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Synthetic Route of 1422-54-4, These common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, 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.

Active magnesium (10 mmol) was added in a RB containing dry THF (10 ml) and added a little iodine and stirred the reaction mixture and to this was added compound 1 (in 2 ml THF) slowly and stirred to generate the Grignard reagent. The reaction mixture was cooled to 0 C. and added compound 2 (in THF) drop wise and stirred the reaction mixture at rt for 2 h. After 2 h the reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer washed with water, brine, dried over sodium sulphate and evaporated under reduced pressure to obtain compound 3.

Statistics shows that 2-Bromo-6-fluorotoluene is playing an increasingly important role. we look forward to future research findings about 1422-54-4.

Reference:
Patent; CELLIX BIO PRIVATE LIMITED; Kandula, Mahesh; US9175008; (2015); B1;,
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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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H15Br

Ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate A mixture of 0.4 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate, 0.245 g of 1-bromo-2-cyclohexylethane, 0.18 g of potassium iodide and 0.737 g of potassium carbonate in 15 cm3 of acetonitrile was stirred for 18 hours at a temperature in the region of 70 C. After cooling to about 20 C., the reaction mixture was concentrated to dryness under reduced pressure (5 kPa) at a temperature in the region of 40 C. The evaporation residue was purified by chromatography under atmospheric pressure, on a cartridge of silica gel (Bond Elut; particle size 70-200 mu; mass 12 g), eluding with a mixture of ethyl acetate/40-60 C. petroleum ether (8/2 by volume). The fractions containing the product were combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40 C. 0.23 g of ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate was obtained. 1H NMR Spectrum (500 MHz, (CD3)2SO-d6, delta in ppm) 0.84 (mt: 2H); 0.98 (t, J=7 Hz: 3H); from 1.00 to 2.65 (mt: 25H); 3.02 (mt: 2H); 3.93 (s: 3H); 3.95 (q, J=7 Hz: 2H); 7.31 (broad s: 1H); 7.35 (broad d, J=9 Hz: 1H); 7.94 (d, J=9 Hz: 1H); 8.67 (broad s: 1H).

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baque, Eric; Carry, Jean-Christophe; El-Ahmad, Youssef; Evers, Michel; Hubert, Philippe; Malleron, Jean-Luc; Mignani, Serge; Pantel, Guy; Tabart, Michel; Viviani, Fabrice; US2002/111492; (2002); A1;,
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Electric Literature of 7073-94-1, These common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, 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.

General procedure: A sealed 10mL glass tube containing substrate 1a-1s (1.5mmol), trimethylsilylacetylene (1.5mmol), triethylamine (7.5mmol), Pd(PPh3)2Cl2 (5mol%), CuI (10mol%), and acetonitrile (1mL) was placed in the cavity of a microwave reactor and irradiated for 2-10min, at 120C and power 150W. After cooling to room temperature by an N2-flow, the tube was removed from the rotor. The reaction mixture was combined with dichloromethane (30mL) and water (30mL). The organic layer was separated and washed with water (2×30mL), dried over sodium sulfate, and concentrated. Purification by column chromatography, eluting with petroleum ether gave 1-aryl-2-(trimethylsilyl)acetylenes (2a-2s) as coloured oils or solids. All the products 2a-2s were characterized by 1H NMR and EI-MS. (See Supporting Information file for characterization data of 1H NMR and EI-MS spectrum.)

The synthetic route of 7073-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lei, Yonghua; Hu, Tianhan; Wu, Xingsen; Wu, Yue; Xiang, Hua; Sun, Haopeng; You, Qidong; Zhang, Xiaojin; Tetrahedron Letters; vol. 57; 10; (2016); p. 1100 – 1103;,
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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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7Br

3-Carboxaldehydebicyclo[4,2,0]octa- 1 ,3;5-triene or A- Carboxaldehydebenzocyclobutene, Q6. To a 500-mL flask was added ’50 mL dry of THF, Mg turnings (2.88 g, 120 mmol), and 1,2-dibromoethane (4 drops). The reaction mixture was then heated under reflux for 15 min, 4-Bromobenzocyclobutene, 5,1 1 (20.0 g, 109 mmol) in 25 mL THF was added via a dropping funnel to form the Grignard reagent. After addition and rinsing the dropping funnel with 25 mL of dry THF, the reaction mixture was heated for an additional 45 min under reflux to give a green brown solution. The reaction mixture was then cooled to 0 0C, DMF (15 mL, 210 mmol) was added dropwise to the solution, and the reaction mixture was heated under reflux for 15 min. The reaction mixture was poured onto 150 g of ice, acidified to pH), and neutralized with saturated NaHCO3 solution. The crude product was extracted with ethyl acetate, the organic phase was filtered over Celite, and evaporation of the solvent gave the crude product. The product was purified by column chromatography using 10% diethyl ether/hexane as eluting solvents and was finally purified by Kugelrohr distillation (145 0C, 0.5 mm) to give the aldehyde Q6 (1 1.7 g, 81.2%) as a colorless liquid; IR 3000-2800, 1690, 1598, 1216, 1067 and 827 CnV1; 1H NMR (400 MHz, CDCl3) delta 9.9 (s, IH, CHO), 7.65 (dd, IH, J= 7.4 Hz, J= 1.2 Hz, ArH), 7:50 (s, IH, ArH), 7.14 (dd, IH, J =7.4 Hz, J) 1.2 Hz, ArH), 3.15 (s, 4H, CH2); 13C NMR (100 MHz, CDCl3) «5 192.28, 153.69, 146.57, 135.4, 130.26, 122.89, 122.81, 29.97, and 29.23. Anal. Calcd for C9H8O; C, 81.8; H 6.10. Found: C, 81.7; H, 5.94.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; WO2008/24435; (2008); A2;,
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Electric Literature of 58534-95-5, 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. 58534-95-5 name is 3-Bromo-2-fluoroaniline, 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.

A solution of 3-bromo-2-fluoroaniline (1.00 g, 5.26 mmol) in formic acid (1.99 mL, 52.6 mmol) was heated at 90 C. for 16 h. The mixture was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed sequentially with saturated aqueous NaHCO3 and brine, dried and concentrated to provide N-(3-bromo-2-fluorophenyl)formamide as a beige solid (1.02 g, 89% yield). Mass spectrum m/z 218, 220 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 8.50 (s, 1H), 8.40-8.17 (m, 1H), 7.53-7.41 (m, 1H), 7.31 (ddd, J=8.0, 6.6, 1.4 Hz, 1H), 7.05 (td, J=8.2, 1.4 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
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Reference of 2924-09-6, 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. 2924-09-6, name is 5-Bromo-2-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: BSB-Cl 2 (314 mg, 1.2 mmol) and aniline 1 (1mmol) were premixed in THF (10 ml) at0 C to which was added LiHMDS (2 ml, 2 mmol). The resulting mixture was stirred for2 h at this temperature. Upon reaction completion, the solution was concentrated. Theresidue was purified with basic alumina flash chromatography to afford pure product

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, 5-Bromo-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lu, Erhu; Yadav, Arun; Weaver, Donald F.; Reed, Mark A.; Synlett; vol. 24; 17; (2013); p. 2259 – 2262;,
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