Category: bromides-buliding-blocks

Reference of 1073-06-9,Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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.

A degassed solution of tert-butyl 4-(2-methyl-5-{4-[4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]butanoylamino}phenyl)piperidine carboxylate (19.0 mg, 0.033 mmol) in dimethylformamide (0.8 mL), was added to a mixture of 3-fluorobromobenzene (6.55 mg, 0.370 mmol), 1,1′-Bis-(diphenylphosphino)-ferrocenedichloropalladium (3.30 mg, 8 mol %) and cesium carbonate solution,(2M, 50 muL) and the resulting mixture was heated in the microwave at 110 C. for 25 min. The reaction mixture was concentrated in vacuo, then partitioned between water (20 mL) and EtOAc (2×10 mL). The organic phase was separated, washed with water (2×20 mL), dried over sodium sulfate and concentrated in vacuo to leave a gum. Purification of the crude product on silica gel (silica gel 60, 20 mL) eluting with cyclohexane:EtOAc, 85:15 then 4:1 gave tert-butyl 4-(5-{4-[4-(3-fluorophenyl)phenyl]butanoylamino}-2-methylphenyl)piperidine carboxylate (13.0 mg, 73%). ESI-MS m/e: 431.3 (M-C5H8O2+H)+.

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-3-fluorobenzene, its application will become more common.

Reference:
Patent; H. Lundbeck A/S; US2005/154022; (2005); A1;,
Bromide – Wikipedia,
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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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

PREPARATION 47 4-(2,2-difluoro-1,3-benzodioxol-5-yl)aniline A solution of 5-bromo-2,2-difluoro-1,3-benzodioxole (2.65 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.97 mmol), tetrakis(triphenylphosphine)palladium(0) (0.08 mmol), and cesium carbonate (7.94 mmol) in N,N-dimethylformamide (8.0 mL) and water (2.0 mL) was heated at 100 C. for 18 h. The reaction mixture was cooled, poured into brine (60 mL), and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a white solid (50%). ESMS [M+H]+: 250.2.

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; Parrish, Cynthia A.; Dhanak, Dashyant; US2007/142460; (2007); A1;,
Bromide – Wikipedia,
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Synthetic Route of 5003-71-4,Some common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, molecular formula is C3H9Br2N, 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.

Step A N-Benzyloxycarbonyl-3-bromopropylamine To a stirred suspension of 3-bromopropylamine hydrobromide (2 g, 9.14 mM) in 40 mL dry THF was added, via hypodermic syringe, benzyl chloroformate (1.64 g, 9.60 mM) at room temperature. After cooling to 0 C., diisopropylethylamine (1.6 mL, 9.20 mM) was added dropwise via syringe and the reaction mixture was allowed to stir at 0 C. for 1 hour. The crude reaction mixture was filtered over a pad of Celite and solvents were evaporated. The residue was flash chromatographed on silica gel, eluding with 10-20-30% EtOAc/hexane to afford 1.56 g desired product as a liquid, homogeneous by TLC in 80:20 hexane-EtOAc; 1 H-NMR (200 MHz, CDCl3, ppm) delta2.06 (m, 2H), 3.37 (m, 4H), 4.92 (br, 1H), 5.10 (s, 2H), 7.34 (s, 5H). Mass spectrum (FAB) m/e 273 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromopropan-1-amine hydrobromide, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5411980; (1995); A;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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 52723-82-7, HPLC of Formula: C7H7BrFN

Acetic anhydride (1.488 mL, 15.77 mmol) was added to a suspension of 4-bromo-5- fluoro-2-methylaniline (1.6087 g, 7.88 mmol) in chloroform (18 mL) under ice-bath cooling and the mixture stirred at RT for 5 min. Potassium acetate (0.812 g, 8.28 mmol), a solution of 18-crown-6 (0.417 g, 1.577 mmol) In chloroform (4 mL) and then t-butyl nitrite (2.186 mL, 16.56 mmol) were then added and the mixture heated at 75°C for 16 h. The dark brown mixture was then cooled, DC (20 mL) added and the organic layer washed with saturated aqueous sodium bicarbonate solution (ca. 20 mL) then reduced. The residue was purified by chromatography on silica gel eluting with a gradient of 0-30percent ethyl acetate in hexane. Impure fractions were purified further by chromatography on silica gel eluting with a gradient of 0-20percent ethyl acetate in isohexane. All pure fractions were combined and then reduced to afford the title compound as a light orange solid (984 mg). 1H N R (CDCl3l 400MHz) delta ppm: 2.79 (3H, s), 7.95 (1 H, dd, 6.5 Hz, 0.5 Hz), 8.07 (1H, d, J 1.0 Hz), 8.25 (1 H, dd, J 9.0, 0.5 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Bromide – Wikipedia,
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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. 553-94-6, name is 2,5-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., name: 2,5-Dimethylbromobenzene

Under argon atmosphere, arylbromides (0.6 mmol), palladium catalyst (0.5 mol%), KOtBu(0.6 mmol) and DMF (5 mL) were added to a schlenck containing a magnetic stir bar, followedby (0.6 mmol) of phenylacetylene. The resulting mixture was placed in an oil bath preheatedto 100 C and stirred vigorously for the indicated time. Upon completion, the mixture wascooled to room temperature, was partitioned between 30 mL of water and 20 mL of diethyletheror ethyl acetate and the combined organic layer was further washed with 2 × 20 mLof diethylether or ethyl acetate and was dried over MgSO4. The extraction was done withDCM when 2,6-dibromopyridine was used as a substrate. The ltrate was sampled at intervalsfor GC analysis to check the purity and the conversions are based on arylbromides.

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:
Article; Boubakri; Mansour; Harrath; Oezdemir; Ya?ar; Hamdi; Journal of Coordination Chemistry; vol. 71; 2; (2018); p. 183 – 199;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 4117-09-3, 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. 4117-09-3, name is 7-Bromo-1-heptene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Synthesis of Nonenoic Acid (Compound 19) Sodium ethoxide was added to a solution of diethylmalonate in ethanol. To this solution was added 1-bromo-hept-6-ene. The reaction mixture was concentrated and then treated with aqueous potassium hydroxide. The reaction mixture was acidified and then heated at 140 C. to ensure decarboxylation and give nonenoic acid (19).

The synthetic route of 7-Bromo-1-heptene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Achillion Pharmaceuticals Inc.; Phadke, Avinash; Hashimoto, Akihiro; US9006423; (2015); B2;,
Bromide – Wikipedia,
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Synthetic Route of 766-81-4, 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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

In 25 ml in the reactor, adding O-bromophenyl (0.034 g, 0.2 mmol) and cuprous iodide (0.004 g, 0 . 02 mmol) butyl potassium (0.045 g, 0.4 mmol), vacuum replace the nitrogen after three times by adding 3 – bromophenylacetic acetylene (0.054 g, 0.3 mmol) and water (0.015 g, 0.8 mmol), in anhydrous 1, 4 – dioxane 1.5 ml, 110 C under stirring 16 h after. Column chromatography (silica gel, 200 – 300 mesh; developing agent, petroleum ether: ethyl acetate=5:1) to obtain 3 – (3 – bromophenylacetic methylene) isoindoline -1 – one 0.042 g, yield 70%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromophenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dalian University of Technology; Bao Ming; Li Pengcheng; Zhang Sheng; Wang Wanhui; (24 pag.)CN109912492; (2019); A;,
Bromide – Wikipedia,
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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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., Product Details of 10269-01-9

Example 1. Synthesis of iV2-{[3′-(aminomethyl)biphenyl-3-yl]methyl}-iV4-{[mM5-4- (aminomethyl)cyclohexyl]methyl}-5-nitropyrimidine-2,4-diamine; To a mixture of 2,6-dichloro-5-nitropyrimidine (17.13 g, 88.30 mmol) and CH3CN (50 mL) at 0 0C was added a mixture of ^ra«5-(4-aminomcthyl-cyclohcxylmcthyl)-carbamic acid tert-butyl ester (21.40 g, 88.30 mmol) and lambdazetaN-diisopropylethylamine (15.4 mL, 88.30 mmol) in CH3CN (50 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. Volatiles were evaporated in vacuo and the residue purified by silica gel chromatography (Hexane/EtOAc 4:1) to afford tr°«5-4-[(2-chloro-5- nitro-pyrimidin-4-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-buty] ester (25.00 g, 71%) as an off-white solid.To a solution of 3-bromo-benzylamine (716 mg, 3.85 mmol) and. diisopropylethylamine (0.65 mL, 3.75 mmol) in dichloromethane (25 mL) was added /ralpha«lambda’-4-[(2-chloro-5-nitro- pyrimidin-4-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-butyl ester (1.01 g, 2.53 mmol). The rxn mixture was stirred at room temperature for 17 h, then partitioned between ethyl acetate and IM HCl solution. The organic phase was washed with satd NaHCtheta3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with 0-3% MeOH in CH2Cl2 to afford 723 mg (52%) of (trans-4-{[2-(3-bromo-benzylamino)-5-nitro-pyrimidin-4- ylamino] -methyl) -cyclohexylmethyl)-carbamic acid tert-butyl ester as a pale yellow solid, m/z 549.3 (M + H)+.To a mixture of (fralphan>s-4-{[2-(3-bromo-benzylam.mo)-5-nitro-pyrimidin-4-ylamino]- methyl}-cyclohexylmethyl)-carbamic acid tert-butyl ester (50 mg, 0.091 mmol), (3- aminomethylphenyl)boronic acid HCl (26 mg, 0.137 mmol), tetrakis(triphenylphosphine)palladium (10 mg, 0.009 mmol), and sodium carbonate (38 mg, 0.360 mmol) was added dimethoxyethane (1.0 mL) and water (0.150 mL). The reaction mixture was sealed under N2 and heated at 90 0C for 5 h. The reaction mixture was partitioned between ethyl acetate (20 mL) and water (5 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with 0-80% 0.1 :1 :9 NH4OH/MeOH/CH2Cl2 in CH2Cl2 to furnish 21 mg (40%) of [?ralphar°-4-({2-[(3′-aminomethyl-biphenyl-3-ylmethyl)- amino]-5-nitro-pyrimidin-4-ylamino} -methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester as a yellow oil, m/z 576.4 (M + H) ‘ . ” A solution of [tralpha«lambda’-4-({2-[(3′-aminomethyl-biphenyl-3-yhnethyl)-amino]-5-nitro- pyrimidin-4-ylamino}-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (21 mg, 0.036 mmol) in dichloromethane (4.0 mL) was treated with 4 M HCl in dioxane (0.100 mL, 0.400 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated. The crude product was purified silica gel chromatography eluting with 0- 100% 0.1:1:9 NH4OH/MeOH/CH2Cl2 in CH2Cl2 to give 16 mg (93%) of N2-{[3′-(aminomethyl)biphenyl-3-yl]methyl} -N4- {[trans-4-(aminomethyl)cyclohexyl]methyl} -5- nitropyrimidine-2,4-diamine, m/z 476.5 (M + H)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/76247; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of bromo-tert- butylbenzene (4.62 g, 21.68 mmol) in THF (50 mL) was cooled to-78 °C then n- BuLi (2.5M, 9.1 mL) was added dropwise. The reaction was stirred for 30 min then a solution of 1-benzyl-piperidin-4-one (3.69 g, 19.5 mmol) in THF (10 mL) was added dropwise. After stirring for 30 min at-78 °C, the reaction was warmed to 0°C then quenched with water (50 mL). The reaction was diluted with ethyl acetate (100 mL); the organic was separated, washed with brine (50 mL), dried over magnesium sulfate and concentrated yielding an oil (6.94 g, 21.5 mmol), which was used in the next step without further purification; LC rt=2.98 min; MS (ESI) 306.2.

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2924-09-6, These common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-fluoroaniline, 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.

A vial was charged with 5-bromo-2-fluoroaniline (1 g, 5.26 mmol), bis(pinacolato)diboron (1.6 g , 6.31 mmol), potassium acetate (1.03 g, 10.52 mmol), Pd(dppf)Cl2 · CH2C12 (129 mg, 0.158 mmol), and DMF (10 mL) under nitrogenatmosphere. After stirring for 2 h at 100 C the reaction mixture was concentrated in vacuo, the residue was triturated with EtOAc and filtered through a pad of celite. The filtrate was adsorbed on silica gel. Purification by flash silica gel chromatography using a gradient of 0- 30% EtOAc/hexane afforded 1.25 g of pinacol 3-amino-4-fluoroboronate as a light yellow oil (quant.): 1H NMR (CDC13, ppm) delta 1.36 (s, 12H), 3.71 (broad s, 2H), 7.00 (dd, 1H), 7.19 (m, 1H), 7.26 (dd, 1H); [M+H]+ m/z 238.

Statistics shows that 5-Bromo-2-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 2924-09-6.

Reference:
Patent; SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-michel; HOPKINS, Stephanie; BOUNAUD, Pierre-Yves; O’CONNOR, Patrick; MATTHEWS, David; BENDER, Steve; WO2012/125981; (2012); A2;,
Bromide – Wikipedia,
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