Category: bromides-buliding-blocks

Some common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-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. Product Details of 2924-09-6

To a stirred solution of chloral hydrate (6.28 g, 37.97 mmol, CAS RN 302-17-0) in water (40 mL) was added Na2504 (43.73 g, 473.68 mmol, CAS RN 7757-82-6) at 25C and the reaction mixture was heated to 35C. Then a warmed mixture of 5-bromo-2-fluoro-phenylamine (6.5 g, 34.21 mmol, CAS RN 2924-09-6), water (40 mL) and concentrated HC1 (6.5 mL) followed by hydroxyl amine hydrochloride (8.08 g, 116.32 mmol, CAS RN 5470-11-1) in water (20 mL)were added to reaction mixture at 35C and reaction mixture was stirred at 90C for 3 h. After cooling to 25C the reaction mixture was filtered, dried and azeotroped with toluene to get the title compound as an off-white solid (7.6 g, 85%). MS (ESI): mlz = 263.1 [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 2924-09-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; (217 pag.)WO2017/137334; (2017); 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. 7051-34-5, name is (Bromomethyl)cyclopropane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (Bromomethyl)cyclopropane

Preparation 4 2-Cvclopropylmethyl-ri,3″|dithiane-2-carboxylic acid ethyl esterTo a flamed dried flask is added dry toluene (80 mL) and sodium hydride (60%, 33.5 mmol, 1.34 g). The reaction is cooled in a ice bath and a solution of ethyl 1,3 dithiane carboxylate (52 mmol, 10 g) and bromomethyl cyclopropane (62.4 mmol, 8.42 g) in DMF (24 mL) are added dropwise over 10 min. The ice bath is removed and the reaction is stirred for 18 h. Water is added (50 mL) and the organic layer is separated. The organic layer is washed with brine, dried (Na2SO4), and concentrated to a yellow oil (12 g, 92 %). LC-MS: 247.0 (M+l).

According to the analysis of related databases, 7051-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 393-37-3, 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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

Compound 28 (200 mg, 0 . 823mmol), compound 29 (86.34 mg, 0 . 549mmol) and K2CO3(227.63 mg, 1 . 647mmol) to 25 ml in two neck bottles, the oil pump and the gas is removed using argon saturated, syringe injection 3ml THF and 1ml H2O, then re-used to remove saturated with argon gas and in the bottle. Slowly adding PdCl2(PPh3)2(38 mg, 0 . 0549mmol), water pump for removing saturated with argon gas and in the bottle. The temperature is increased to 70 C, stirring reflux 2h. The reaction solution with ethyl acetate extraction 3 time, combined with the organic layer, anhydrous Na2SO4drying, concentration. Column chromatography PE_EA= 100:1 to 120 mg white solid 3, yield 53%

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

Reference:
Patent; SICHUAN BAILI PHARMACEUTICAL CO LTD; WU, YONG; ZHU, YI; HAI, LI; LI, JIE; YU, YONGGUO; LIU, WEIJIA; (26 pag.)CN103804312; (2016); B;,
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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 39478-78-9

5-bromo-2-methyl-4-nitroantine Two duplicate reactions were carried out in parallel: To a 3-necked 3 L flask was added H2SO4 (1.25 L). The flask was cooled to 0C. Then, 5-bromo-2-methylaniline (250 g, 1.34 mol) was added followed by the portion- wise addition of KNO3 (135.8 g, 1.34 mol). The solution was stirred at 20C for 3 hours. The crude reaction was then added to 10 L of ice water and a solid precipitated. The solid was filtered off to afford intermediate B.l, (5-bromo-2-methyl-4-nitroaniline after combining material from the duplicate reactions. The crude material was used directly for subsequent steps without additional purification.

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; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Bromide – Wikipedia,
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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. 608-30-0, name is 2,6-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H5Br2N

General procedure: A flask equipped with a septum and a stirring bar was charged with aniline derivative (2.00 g, 1.00 equiv). The flask was closed andTHF (5 mL) was added by using a syringe under an argon atmosphere.The solution was cooled to -20 C and BF3*OEt2(1.50 equiv) was added. Isoamyl nitrite (1.50 equiv) was then slowly added under vigorous stirring and the solution was stirred for 2 hat this temperature. The precipitate was filtered off and washed withice-cold Et2O. Without further isolation, the precipitate was then poured (with MeCN wash) into a freshly a prepared solution containing i-Pr2NH (3.00 equiv) in a mixture of THF-pyridine (9:1, 10 mL) at -20 C. The solution was stirred and allowed to warm slowly to r.t. for an additional 16 h. The reaction was then quenched with sat. NH4Cl solution, the aqueous phase was extracted twice with EtOAc and the organic layer was dried over MgSO4. The solvent was removed in vacuum and the crude product was purified by flash column chromatography (silica gel).

The synthetic route of 608-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Review; Hafner, Andreas; Hussal, Christoph; Braese, Stefan; Synthesis; vol. 46; 11; (2014); p. 1448 – 1454;,
Bromide – Wikipedia,
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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 4117-09-3 as follows. Computed Properties of C7H13Br

A clean, dry, 1 L 3-neck flask equipped with a stir bar and nitrogen inlet was charged with magnesium turnings (10.31 g, 0.4241 mol, 1.5 equiv.) and ?0.1 mg of iodine, and the flask was purged with nitrogen for 5 minutes. 750 mL of anhydrous THF [15 mL/g of 7-bromohept-1-ene (3)] was charged and stirring was initiated. 7-Bromohept-1-ene (3, 50.02 g, 0.2824 mol, 1.0 equiv.) was slowly added drop wise over 10-15 minutes under nitrogen. During this period, the pink color of iodine disappeared during initial stages, the reaction was found to be slightly exothermic, and the temperature of the contents was raised from an initial ambient (20-23 C.) to about 31 C. After the addition was complete, the resulting pale gray color solution was cooled to room temp (23 C.) and stirring was continued for an additional 2.5 h under nitrogen to form the Grignard reagent (7-hept-1-ene magnesium bromide). Into a separate 2 L dry three neck RB flask equipped with a mechanical stirrer, thermocouple and an addition funnel with nitrogen inlet, diethyl oxalate (4, 82.61 g 0.5642 mol, 2.0 equiv.) and 750 mL of anhydrous THF [15 mL/g of 7-bromo-1-pentene (3)] were charged under nitrogen. The mixture was cooled to below -20 C. temperature (Jacket temperature: -23 C.) with stirring. The Grignard reagent (7-hept-1-ene magnesium bromide), which was prepared as described above, was transferred using a cannula into a side-arm addition funnel set on top of the 2 L RB flask. The reagent was added drop wise slowly into diethyl oxalate-THF solution over 1 h 50 min, while maintaining the jacket temperature below -23 C. During the addition of the Grignard reagent, the reaction was found to be exothermic and the internal temperature was raised to maximum of -18 C. After the addition was complete, the mixture was warmed to -15 C., and the progress of the reaction was monitored by HPLC. After 3 h at -15 C., the reaction mixture was warmed to -10 C., quenched with 3N hydrochloric acid solution and the final pH was adjusted to 1.4-1.6 by drop wise addition. During the quench, the internal temperature rose to -6.7 C. due to an exotherm while, the jacket temperature was maintained at -12 C. The mixture was stirred for an additional 10 min and the pH was re-checked and confirmed to be approximately, 1.7-1.8. The mixture was warmed to 22 C., and the pH was again re-checked (pH=2.8) and re-adjusted to pH=1.2 with 3N hydrochloric acid solution. A total of 81 mL of 3N hydrochloric acid solution was used for quench and pH adjustment. Agitation was stopped and the layers allowed to settle. The organic phase was separated, and the bottom aqueous layer was back-extracted with dichloromethane (1*100 mL). The combined organic phases were concentrated on a rotary evaporator (Bath temperature: 45 C./Vacuum) to give the crude product as a yellow oil. The crude product was dissolved in 200 mL of dichloromethane (some solids/salts were present) and 200 mL water. The bottom aqueous phase was separated and back-extracted with dichloromethane (2*200 mL). The combined organic phases were dried over anhydrous magnesium sulfate (25 g), filtered and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), to afford a pale yellow viscous as oil. The crude product was purified by flash chromatography in four equal portions, with each portion dissolved in about 25 mL of dichloromethane for loading onto a silica gel column and eluted using 5-10% ethyl acetate in hexanes. The selected fractions were combined and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), and further dried under vacuum (<5 mm/Hg) at ambient temperature for 4 h to afford 36.49 g of ethyl 2-oxonon-8-enoate (5) in 65.2% yield as colorless oil. According to the analysis of related databases, 4117-09-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; AbbVie Inc.; Abrahamson, Michael J.; Pruyne, Julie J.; Kielbus, Angelica B.; Lallaman, John E.; Reddy, Rajarathnam E.; Chemburkar, Sanjay R.; (29 pag.)US10059969; (2018); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, 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 174508-31-7, Computed Properties of C6H4Br2O2S

2,5-Bis(thieno[3,2-b]thiophen-2-yl)-2-3,4-ethylenedioxythiophene(TT-EDOT-TT).

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, 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xue, Yu; Xue, Zexu; Zhang, Wenwen; Zhang, Wenna; Chen, Shuai; Lin, Kaiwen; Xu, Jingkun; Polymer; vol. 159; (2018); p. 150 – 156;,
Bromide – Wikipedia,
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Reference of 3814-30-0, A common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

To a solution of ethyl 9′-hydroxy-1 0′-methyl-2′-oxo-2′,7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3′-carboxylate (90 mg, 0.265 mmol)in DMF (5 ml) was added K2C03 (73.2 mg, 0.530 mmol) and (bromomethyl)cyclopentane(51.8 mg, 0.318 mmol). The mixture was heated at 90 oc for 3 hours. The mixture wascooled to room temperature and partitioned between EtOAc and H20. The organic layerwas separated and the aqueous layer was extracted 2 times with EtOAc. The combinedorganic layers were washed brine, filtered, concentrated, and the residue purified by flashedchromatography (silica gel, 0-20 % MeOH in DCM to afford ethyl 9′-(cyclopentylmethoxy)-1 0′-methyl-2′-oxo-2′, 7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3’carboxylate(60 mg, 53.7% yield). LCMS (ESI) m/z: 422.4 (M + 1t.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 327-51-5,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.

Under an argon atmosphere, to a solution of 1,4-dibromo-2,5-difluorobenzene (1) (20.00 g, 73.6mmol) in diethyl ether (160 mL) was added dropwise 1.6 M n-butyl lithium solution in hexane(1.05 eq, 49 mL) at -78 C, and the mixture was stirred at same temperature for 2 min. Themixture was added quickly to the mixture of dry ice (about 100 g) and diethyl ether (200 mL),and the mixture was warmed up to room temperature. The precipitate was collected by filtration, and washed with diethyl ether. The obtained solid was treated with water (50 mL) and 1 M hydrochloric acid (150 mL), and extracted with diethyl ether. The organic layer was washed with brine and dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was washed with hexane, dried in vacuo to obtain 4-bromo-2,5-difluorobenzoic acid ( 14.8 g, 85 percent) as a pale yellow solid: 1H NMR (DMSO-d6) delta 7.78(1H, dd, J = 6.4, 8.3 Hz), 7.89 (1H, dd, J = 5.9, 9.8 Hz).

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

Reference:
Article; Wood, Martyn; Ates, Ali; Andre, Veronique Marie; Michel, Anne; Barnaby, Robert; Gillard, Michel; Molecular Pharmacology; vol. 89; 2; (2016); p. 303 – 312;,
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. 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, A new synthetic method of this compound is introduced below., COA of Formula: C12H8Br2

The preparation method of the raw material A (4,5-dibromoacenaphthene) is as follows: In a 1000 mL two-necked flask, 18.72 g (60 mmOl) of 4,5-dibromofluorene and 500 mL of acetic anhydride were added, stirred and heated to 110 C, and a solution of chromium trioxide in acetic anhydride (46.4 g of three) was slowly added dropwise over about two hours. The chromium oxide is dissolved in 300 mL of acetic anhydride). After the completion of the dropwise addition, the temperature was raised to 160 C and the reaction was continued for 30 minutes. After the reaction was completed, the reaction solution was poured into a beaker containing 1000 g of crushed ice, and stirred to dissipate heat, and then 20 mL of concentrated hydrochloric acid was slowly added dropwise, and the mixture was decompressed. After filtration, a yellow solid was obtained, then the residue was recrystallized from acetic acid, and filtered, and then filtered to give a dark brown solid 5.21 g, yield: 25·54%.

The synthetic route of 19190-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary