Category: bromides-buliding-blocks

Some common heterocyclic compound, 2550-36-9, name is (Bromomethyl)cyclohexane, molecular formula is C7H13Br, 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. COA of Formula: C7H13Br

General procedure: In Example 1, 17.98 g (108.95 mmol) of 1-bromohexane,(Bromomethyl) cyclohexane 19.29 g (108.95 mmol), In the same manner as in Example 1,19.74 g of Compound 5 was obtained as white crystals. The results are summarized in Table 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2550-36-9, its application will become more common.

Reference:
Patent; ZEON CORPORATION; JAPAN FINECHEM INCORPORATED; SANUKI, KANAKO; OKUYAMA, KUMI; SATO, KOKI; TAMAKI, RYUSUKE; KURODA, TOSHIHIRO; SUZAKI, DAISUKE; (19 pag.)JP2016/190818; (2016); A;,
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These common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. HPLC of Formula: C6H2BrF3

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (3.46 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (3.98 g, 0.011 mol, yield 73%). 1H NMR (400 MHz, CDCl3) delta 7.01 (t, J=10.5 Hz, 1H), 6.926.88 (m, 1H), 5.14 (d, J=12.6 Hz, 1H), 4.50 (s, 2H), 3.953.85 (m, 1H), 3.823.77 (m, 1H), 3.773.55 (m, 1H), 3.40 (s, 3H), 2.82 (s, 2H), 1.871.68 (m, 1H), 1.631.48 (m, 1H), 1.39 (s, 9H). Ms (M++1): 364.

The synthetic route of 1-Bromo-2,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
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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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

Example 76 [(S)-(3-(4-N-Neopentyl-N-piperazinyl)propylthio)methyl-Sar] -3- [(y-hydroxy)-NMeLeu] – -cyclosporin [0243] [(S)-3-(N-Piperazinylpropylthio)methyl-Sar]-3-[(Y-hydroxy)-N-MeLeu]-4- cyclosporin (150 mg, 0.11 mmol) and neopentyl bromide (MW 151.05, d 1.195, 136 mu, 1.08 mmol) were dissolved in dichloromethane (20 ml), followed by adding sodium carbonate (MW: 105.99, 28.6 mg, 0.27 mmol). The mixture was stirred at room temperature overnight. Then the reaction mixture was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using dichloromethane and methanol as eluent to give product [Molecular Formula: C75H137N13O13S; Exact Mass: 1460.02; MS (m/z): 1460.64 (M+l)+, 1482.72 (M+Na)+; TLC Rf: 0.43 (dichloromethane/methanol = 9: 1); HPLC RT: 11.25 min (C8 reverse phase column: 250 mm; acetonitrile/water (0.05% trifluoroacetic acid); operation temperature: 64 C; detector: 210 nm)].

The synthetic route of 630-17-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SU, Zhuang; LONG, Zhengyu; YANG, Suizhou; WO2014/145686; (2014); A2;,
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Synthetic Route of 4549-33-1,Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

1,9-Dibromononane (610 muL, 3 mmol) was added to a stirred solution of the product of Preparation 1 (377 mg, 1 mmol) and DIPEA (1.05 mL, 6 mmol) in DMF (5 mL) at 50 C. The reaction mixture was heated at 80 C. for 72 h and then the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (10% MeOH in DCM containing 0.5% NH4OH) to give the title compound (292 mg, 0.5 mmol, 50%).

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

Reference:
Patent; Mammen, Mathai; Hughes, Adam; US2004/242622; (2004); A1;,
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Application of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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: To a flame dried, 3 times evacuated and argon purged 25mL Schlenk flask was added 4.6mmol of aryl bromide (2-bromo-9,9-dimethylfluorene, 9-bromoanthracene, and 1-bromo-4-methylnaphthalene) and a magnetic stir bar. The flask was then cooled to -78 C (dry ice/acetone bath) for 10min under argon (room temperature for phenylacetylide). Then 10mL of dry argon purged diethyl ether was added to the reaction and allowed to cool for another 10min. This was followed by 2.2mL (5.5 mmol) of n-butyllithium solution in diethyl ether. The reaction was allowed to stir for 30min to complete the halide-exchange reaction, at which time the reactions turned a yellow color and salt precipitates formed. Then 1 g (3.8mmol) of spirosiloxane I dissolved in 5mL of cooled dry argon purged diethyl ether was added by syringe to the reaction mixture and allowed to stir for an additional 2 h. The reaction was run till the yellow color subsided and was then quenched with excess Me3SiCl and allowed to stir cold for >30min before warming up. The reaction was then worked up by a quick water wash (2 times) to remove salts and then dried over MgSO4. The reaction was then filtered through Celite to remove salts and solvent removed in vacuo. Yellow-orange viscous oils were obtained. Characterization is given in tabular form in the text.

The synthetic route of 6627-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Furgal, Joseph C.; Laine, Richard M.; Bulletin of the Chemical Society of Japan; vol. 89; 6; (2016); p. 705 – 725;,
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Reference of 69272-50-0, These common heterocyclic compound, 69272-50-0, name is 3,6-Dibromobenzene-1,2-diamine, 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.

3,6-Dibromobenzene-1,2-diamine with round flask equipped with a condenser (compound 2-a) (1g) and phenanthrene-9,10-dione (0.8 g) after the into the respective acetate, 30mL ethanol and 30 after the injection, each mL, was added the temperature to 80 C, and reacted for 24 hours. If after the completion of the reaction through the methanol, the resulting solid filter using methanol to afford a yellow solid 10,13-dibromodibenzo [a, c] phenazine (compound C). (Yield: 68%).

Statistics shows that 3,6-Dibromobenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 69272-50-0.

Reference:
Patent; Pusan National University Industry-Academic Cooperation Foundation; Hwang, Do Hun; Kim, Ji Hun; Kim, Hee Woon; Im, Jong Min; (52 pag.)KR101495152; (2015); B1;,
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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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2,2-dimethylpropane

Lambda/-(1 -Methylcyclopropyl)-3-((3-methylisoxazol-5-yl)methyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-6-sulfonamide (100 mg, 0.260 mmol), cesium carbonate (100 mg, 0.3100 mmol), sodium iodide (8 mg, 0.05 mmol) and 1 -bromo-2,2-dimethylpropane (426 mg, 2.8 mmol) in DMF (2 mL) was heated by microwave irradiation to 130 C for 1 .5 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 20 mL). The organic phase was combined, washed with brine (10 mL), passed through a hydrophobic frit and evaporated to dryness. The crude product mixture was purified by prep HPLC (high pH) to give the desired product (14 mg, 0.03 mmol, 12%) as an off-white powder

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; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
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Synthetic Route of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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 1: tert-Butyl 3-bromo-5-(tert-butyl)benzoate (11a) n-Butyl lithium (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a 100 mL flask under nitrogen atmosphere containing 9 mL of toluene at -10C. n-Butylmagnesium chloride (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min. To this slurry was added 1,3-dibromo-5-(tert-butyl)benzene (6.2 g, 21.2 mmol) dissolved in 20 mL of toluene. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in 7.5 mL of toluene was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 40 mL of a 10% (w/w) aqueous solution of citric acid, which resulted in an exothermic generation of carbon dioxide. The phases were separated and the organic layer was washed with another 40 mL of citric acid solution. The organic extracts were then dried with MgSO4 and the solvents were removed at reduced pressure. Compound 11c was obtained as a brown oil (4.0 g, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); 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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2051-99-2

Intermediate A6 2-(4-isobutylphenyl)-6-methoxy-3.4-dihvdroisoquinolin-l(2H)-one vial, 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.25 g, 1.411 mmol) was dissolved in N-dimethylformamide (2.82 ml). To this was added l-bromo-4-isobutylbenzene (0.451 g, 2.116 mmol) and potassium carbonate (0.390 g, 2.82 mmol). The reaction mixture was flushed with nitrogen, charged with copper(I) iodide (0.161 g, 0.847 mmol) and heated to 150 C for 24 h. The reaction mixture was cooled to room temperature, quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-75% ethyl acetate in heptanes to afford the desired product (190 mg, 0.614 mmol, 43.5 % yield) as a light orange solid. NMR (400 MHz, Chloroform-d) delta 8.12 (d, J = 8.7 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.24 – 7.15 (m, 2H), 6.89 (dd, J = 8.7, 2.6 Hz, 1H), 6.77 – 6.65 (m, 1H), 3.96 (dd, J = 7.0, 6.0 Hz, 2H), 3.86 (s, 3H), 3.09 (t, J = 6.4 Hz, 2H), 2.50 (d, J = 7.1 Hz, 2H), 1.90 (dh, J = 13.5, 6.8 Hz, 1H), 0.94 (d, J = 6.6 Hz, 6H). LC MS (m/z, MH+): 310.4.

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 2051-99-2.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
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Related Products of 4333-56-6, These common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, 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 stirred suspension of potassium fert-butoxide (8.00 g, 71.33 mmol) in DMSO (70 mL) under nitrogen was added 3-mercaptophenol (5 g, 39.63 mmol) at 0 C; the reaction was stirred at room temperature for 30 min. Then bromocyclopropane (5.72 mL, 71.33 mmol) was added into the reaction mixture. The reaction was heated at 90C overnight. After the reaction was completed, it was diluted with EtOAc. The organic layer was washed with water, saturated NH4CI aqueous solution (2x), and brine. The aqueous layer was back extracted with EtOAc (lx). The combined organic layers were dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound (6.19 g, 85% yield). LCMS m/z = 167.2 [M+H]+; NMR (400 MHz, CDCI3) delta ppm 0.68-0.74 (m, 2H), 1.05-1.12 (m, 2H), 2.13-2.22 (m, 1H), 4.75 (s, 1H), 6.60 (dt, / = 8.08, 1.26 Hz, 1H), 6.89 (t, 7 = 2.27 Hz, 1H), 6.93 (ddd, 7 = 7.83, 1.64, 0.88 Hz, 1H), 7.15 (t, 7 = 7.96 Hz, 1H

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; DO, Quyen-Quyen; ULLMAN, Brett; (259 pag.)WO2017/214002; (2017); A1;,
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