Category: bromides-buliding-blocks

4117-09-3, name is 7-Bromo-1-heptene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 7-Bromo-1-heptene

(a) 1-Bromo-6,7-epoxyheptane STR24 37.3 g of 1-bromo-6-heptene were added dropwise with 40 minutes, with stirring and flushing with nitrogen, to 50.9 g of m-chloroperbenzoic acid (85% pure) in 300 ml of methylene chloride at room temperature. After standing overnight, the precipitate was filtered off with suction and the filtrate was washed with 10% strength Na2 S2 O4 solution, with saturated sodium bicarbonate solution and with water and (after drying) evaporated under reduced pressure. 42.2 g of crude 1-bromo-6,7-epoxyheptane were obtained.

The synthetic route of 4117-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4616020; (1986); A;,
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Synthetic Route of 67567-26-4, These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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-2,6-difluoro-phenylamine (1 g, 4.80 mmol) was dissolved in tetrahydrofuran (15 mL) and sodium hydrogen carbonate (483 mg, 5.76 mmol) was added dropwise at 0 C. Benzyl chloroformate (800 mg, 5.76 mmol) was added dropwise and the mixture was stirred at room temperature for 12 hours. Water was added to terminate the reaction and the mixture was washed with diethylether, water and saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous magnesium sulfate, distilled under reduced pressure and separated by column chromatography using 6:1 mixture solution of hexane and ethyl acetate to obtain the title compound (1.3 g, 81 % yield).[407] NMR: 1H-NMR(CDCl3) 7.39~7.34(5H, m), 7.17~7.13(2H, m), 6.07(1H, s), 5.21(2H, s)

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG LIFE SCIENCES LTD.; KIM, Young Kwan; JOO, Hyun Woo; KIM, Myoung Yeol; PARK, Heui Sul; LEE, Tae Hee; KWAK, Hyo Shin; SHIM, Dong Sup; CHOI, Eun Sil; WO2012/111995; (2012); A1;,
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Synthetic Route of 39478-78-9, The chemical industry reduces the impact on the environment during synthesis 39478-78-9, name is 5-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

(1-1) Synthesis of 2-Methyl-5-Phenylaniline A mixture of 5-bromo-2-methylaniline (10.0 g), phenylboronic acid (8.52 g), tetrakis(triphenylphosphine)palladium (0) (1.86 g), a 2 M sodium carbonate aqueous solution (80.6 mL), and 1,2-dimethoxyethane (DME) (135 mL) was refluxed for 5 hours in an argon atmosphere. The resulting reaction mixture was cooled to room temperature, and extracted with dichloromethane. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude 2-methyl-5-phenylaniline was used directly for the subsequent step.

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

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; ITO, Hirokatsu; KAWAMURA, Masahiro; MIZUKI, Yumiko; HAKETA, Tasuku; HAYAMA, Tomoharu; TAKAHASHI, Ryota; (141 pag.)US2017/183291; (2017); A1;,
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Related Products of 134168-97-1, The chemical industry reduces the impact on the environment during synthesis 134168-97-1, name is 3-Bromo-5-fluoroaniline, I believe this compound will play a more active role in future production and life.

Intermediate S2: 3-bromo-5-fluorobenzene-1-sulfonyl chloride To a solution of 3-bromo-5-fluoroaniline (0.500 g, 2.63 mmol) in glacial acetic acid (0.70 mL) cooled in an ice bath, concentrated hydrochloric acid (2.15 mL) was added. Then, a solution of sodium nitrite (0.199 g, 2.89 mmol) in water (0.45 mL) was slowly added maintaining the temperature around 0 C. After completion of the addition, the reaction mixture was further stirred for 20 min. The resulting solution was slowly added to a freshly prepared mixture of aqueous ?40% sodium bisulfite solution (1.915 mL, 7.36 mmol), copper chloride (0.052 g, 0.526 mmol), glacial acetic acid (5.0 mL) and concentrated hydrochloric acid (1 mL) at room temperature and the reaction was stirred at RT for 2.5 h. The mixture was then cooled to 0 C., additional sodium nitrite (0.5 eq) was added and the stirring was continued at r.t. for 1 h. The mixture was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to afford title compound which was used without any additional purification (0.450 g, 1.65 mmol, 63% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.54-7.58 (m, 1H), 7.50-7.54 (m, 1H), 7.30-7.36 (m, 1H).

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
Bromide – Wikipedia,
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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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 38573-88-5

To a solution of Intermediate 37b (20.00 mg, 38.56 muiotaetaomicron) and l-bromo-2,3-difluoro- benzene (22.33 mg, 115.68 muiotaetaomicron, 12.98 pL) in CH3CN (500 pL) was added Cs2C03 (50.25 mg, 154.24 muiotaetaomicron) and XPhos Pd G3 (3.26 mg, 3.86 muiotaetaomicron). After stirring under N2 atmosphere at 70C for one hour, the reaction mixture was purified by prep-TLC (DCM: MeOH = 10: 1) to give the Intermediate 38b (15.00 mg, 23.78 muiotaetaomicron, 61.68% yield) as a yellow 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 38573-88-5.

Reference:
Patent; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; COMER, Eamon; KATO, Nobutaka; MORNINGSTAR, Marshall; MELILLO, Bruno; (154 pag.)WO2018/175385; (2018); 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. 656-64-4, name is 3-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Bromo-4-fluoroaniline

EXAMPLE 48 4-(3-Bromo-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile A mixture of 3.52 g (9.7 mmol) of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile and 2.0 g (10.7 mmol) of 3-bromo-4-fluoro aniline in 150 ml of methoxyethanol was refluxed under nitrogen for 5.5 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried with sodium sulfate and then solvent was removed under vacuum. The residue was chromatographed on silica gel eluding with mixture of ethyl acetate and hexane to give the title compound.

According to the analysis of related databases, 656-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US6297258; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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 399-94-0, Product Details of 399-94-0

To a solution of 2-bromo-1,4-difluorobenzene (1 g, 5.18 mmol) in THF (25 mL) was added LDA solution (2 M in THF, 2.9 mL, 5.8 mmol) dropwise at -78 C. After stirring for 1 h at -78 C., DMF (0.441 mL, 6.03 mmol) was added dropwise and the resulting reaction mixture was stirred at -78 C. for additional 30 min. The reaction was quenched by sat. NH4Cl solution (40 mL) carefully and the mixture was extracted with EtOAc (80 mL*2). The combined organic phase was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 2-bromo-3,6-difluorobenzaldehyde as light brown solid (1.05 g, 92%, crude yield) which was used in next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,5-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
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bromide – Wiktionary

Application of 699-03-6, 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. 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To an oven dried 10 mL screw cap vial equipped with a stir-bar and charged with amine 1a (0.5 mmol) was added aldehyde 2a (84 mg, 1.5 equiv) and toluene (0.2 mL) and the mixture was stirred for 5 min at room temperature. Thereafter, heteroarene 3a (88 mg, 1.2 equiv) and CuCl (10 mg, 20 mol%) were added and the vial was sealed with a Teflon cap. The reaction mixture was irradiated for 50 min at a preselected temperature of 140 oC, with a maximum irradiation power of 200 W. After completion of the reaction, the resulting mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude sample was purified by silica gel column chromatography (10-20% ethyl acetate in heptane) to obtain compound 4a (127mg, 78% yield).

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vachhani, Dipak D.; Sharma, Abhishek; Van Der Eycken, Erik; Angewandte Chemie – International Edition; vol. 52; 9; (2013); p. 2547 – 2550; Angew. Chem.; vol. 125; 9; (2013); p. 2607 – 2610,4;,
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Related Products of 4549-33-1, These common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, 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.

2,2, 12, 12-Tetramethyltridecanedioic acid diethyl ester (153).; Under N2 atmosphere and at-78 C, a solution of lithium diisopropylamide (2 M in heptane/THF/ethylbenzene, 52.5 mL, 105 mmol) was added dropwise to a solution of ethyl isobutyrate (17.4 g, 150 mmol) in THF (50 mL). The mixture was stirred for 1 h and 1, 9-dibromononane (151, 14.3 g, 50 mmol) was added, followed by DMPU (4.4 g, 34.3 mmol). The mixture was stirred for 30 min and the cooling bath was removed. After 30 min, the THF was evaporated under reduced pressure. The residue was diluted with saturated NH4CI ‘bluti6’n” (300 mL) aSd’-exti’Scted with ethyl acetate (3 x l00 mL). The combined organic layers was washed with brine (200 mL), 5 % aqueous HC1 (100 mL) and saturated NaHC03 solution (50 mL), and dried over Na2S04. The solvent was removed under reduced pressure and the residue was distilled in high vacuo to give 153 (14.0 g, 79 %) as an oil. Bp 150-151 C/0. 1 mmHg. 1H NMR (CDC13) : 8 (ppm): 4.08 (q, J= 7. 2, 4 H), 1.48-0. 98 (m, 18 H), 1.21 (t, J= 7.2, 6 H), 1.12 (s, 12 H). 13C NMR (CDCl3) : 5 (ppm) : 178.1, 60.0, 42.1, 40.7, 30.0, 29.4, 25.1, 24. 8, 14.2.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ESPERION THERAPEUTICS, INC.; WO2005/68410; (2005); A1;,
Bromide – Wikipedia,
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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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromodibenzo[b,d]furan

Into a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser fitted with a calcium chloride tube, a nitrogen inlet tube, a 200 mL isobaric dropping funnel and a thermometer, 34.5 g of the bromide obtained in the above (139.6 mmol) of dehydrated THF and 325 mL of dehydrated THF, and the mixture was cooled to -60 ° C. or lower in an acetone-dry ice bath under a nitrogen stream. Subsequently, 106 mL (167.6 mmol) of n-BuLi was added dropwise at -50 ° C. or lower, then the isobaric dropping funnel was washed with 100 mL of THF and added to the reaction solution. Subsequently, after postreaction at -50 ° C. or lower for 1 hour, 43 mL (181.6 mmol) of [B (i-PrO) 3] was added dropwise at -45 ° C. or lower. Subsequently, the isobaric dropping funnel was washed with 80 mL of THF and added to the reaction solution, followed by stirring at -45 ° C. or lower for 30 minutes. The acetone-dry ice bath was removed, the temperature was returned to room temperature, and the reaction was continued for additional 20 hours to obtain boron To obtain a reaction solution.Next, 24 mL of concentrated hydrochloric acid and 241 mL of water were placed in a 1 L four-necked round bottom flask equipped with a stirring device, a Liebig condenser (not required), a 1 L dropping funnel and a thermometer, ° C. Subsequently, the boron reaction solution was dropped at a temperature not exceeding 10 ° C., and the mixture was stirred at 10 ° C. or less for 1 hour, then returned to room temperature and stirred for 3 hours.The obtained reaction solution was transferred to a 1 L separating funnel, the organic layer was separated, and the aqueous layer was extracted with 340 mL of ethyl acetate. Next, the organic layers were combined and washed with saturated brine 240 mL, dried over magnesium sulfate, magnesium sulfate was removed by suction filtration, and the solvent was distilled off under reduced pressure. Subsequently, 220 mL of n-heptane was added to the obtained crude crystals, rinsed at 50 ° C. for 1 hour, cooled to room temperature and filtered by suction to obtain 21.6 g of the desired boronic acid (yield 72.8percent)

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 50548-45-3.

Reference:
Patent; YAMAGATA UNIVERSITY; CHEMIPRO KASEI KAISHA LIMITED; KIDO, JUNJI; SASABE, HISAHIRO; TAKAHASHI, JUN; NAGAI, NAGAI; (723 pag.)JP2018/90561; (2018); A;,
Bromide – Wikipedia,
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