Tag: M.W=200-300

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. Product Details of 327-52-6

This example illustrates step 2 of the process of the invention: Heck coupling of 1-bromo-2,4,5-trifluorobenzene with 1-benzyl-4-methyl-2-methylenesuccinate with selective formation of (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, compound (IV). [Show Image] A 1000 mL round bottomed flask fitted with magnetic stirrer, thermometer, nitrogen inlet and reflux condenser is charged with 1-benzyl-4-methyl-2-methylenesuccinate (100.0 g, 0.43 mol), 1-bromo-2,4,5-trifluorobenzene (124.0 g, 0.59 mol), methyl dicyclohexyl amine (127.0 g, 0.65 mol), dimethyl acetamide (215 mL), water (53 mL) and lithium bromide (7.5 g, 0.09 mol). The mixture is degassed with three vacuum-nitrogen cycles; palladium acetate (260 mg, 1.16 10-3 mol) is then added as reaction catalyst. The mixture is heated with stirring at 95-98 C for 22 hours monitoring by GC until > 95% conversion, then cooled to room temperature, added of water (500 mL) and toluene (250 mL) and filtered on a Celite pad. The organic phase is washed with 1N HCl (200 mL), dried by azeotropic distillation under reduced pressure, treated with coarse silica gel (20 g), filtered and concentrated to a residue (128 g). Gas-chromatographic analysis of the crude product shows the following composition: 87% (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, 7% (Z)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, 4% (E)- and (Z)-1-benzyl-4-methyl 2-(2,4,5-trifluorobenzyl)maleate, 2% starting material. An analytical sample of pure (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate is obtained by flash chromatography with gradient elution 0?20% AcOEt in hexane. 1H NMR (300 MHz, CDCl3) delta 7.77 (s, 1H), 7.40-7.34 (m, 5H), 7.22 (ddd, J=15.3, 8.6, 6.7 Hz, 1 H), 6.97 (ddd, J=15.9, 15.9, 6.4 Hz, 1 H), 5.26 (s, 2H), 3.66 (s, 3H), 3.43 (s, 2H).

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

Reference:
Patent; Chemo Iberica, S.A.; EP2423178; (2012); A1;,
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These common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, 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. SDS of cas: 57946-63-1

A solution of 2-bromo-4-(trifluoromethyl)aniline(5g, 20.83 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (6.34g, 20.83 mmol), and sodium carbonate(5.52g, 52.1 mmol) in toluene (30 ml) / water (20 ml) Ethanol (10 ml), N2 was purged for 10 mm. then Tetrakistriphenyl phosphinePd (0) (2.407g, 2.083 mmol) was charged and stirred at 95 ¡ãC for 4h. After completion of reaction as indicated by TLC, the mixture was poured into water and extracted with ethyl acetate. The organic layer was collected anddried over sodium sulphate, finally evaporated and purified by column chromatography(4.5g, 64 percent). LCMS (ESI): m/z 338.10(M+H).

The synthetic route of 2-Bromo-4-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUPIN LIMITED; RAMDAS, Vidya; LORIYA, Rajeshkumar, Maganlal; BANERJEE, Moloy; PATIL, Pradeep, Rangrao; JOSHI, Advait, Arun; DATRANGE, Laxmikant, Shamlal; WALKE, Deepak, Sahebrao; KHAN, Talha, Hussain; DAS, Amit, Kumar; GOTE, Ganesh, Navinchandra; KALHAPURE, Vaibhav, Madhukar; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (234 pag.)WO2017/37682; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 698-00-0, name is 2-Bromo-N,N-dimethylaniline, 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 698-00-0, Recommanded Product: 698-00-0

General procedure: Bromo-N,N-dimethylaniline (400 mg, 2.0 mmol), (trimethylsilyl)acetylene (236 mg, 2.4 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), CuI (19mg, 0.1 mmol), diisopropylamine (5 mL) and toluene (15 mL) wereadded to a flask and the mixture was stirred at 80 C overnight. Thenthe reaction mixture was poured into saturated NH4Cl (50 mL) andextracted with CH2Cl2 (3 x 20 mL), the organic layer was washed withsaturated brine (1 x 50 mL) and dried over MgSO4. After filtration,solvents were removed by rotary evaporation (40-45 C ). The crudeproduct was subjected to column chromatography (SiO2; eluent,hexane/ CH2Cl2, 3:1) to give the corresponding compounds. N,N-Dimethyl-2-[(trimethylsilyl)ethynyl]aniline (3c): Pale yellow oil; yield 81%.

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Reference:
Article; Fang, Jing-Kun; Sun, Tengxiao; Fang, Yu; Xu, Zhimin; Zou, Hui; Liu, Yuan; Ge, Fangting; Journal of Chemical Research; vol. 39; 8; (2015); p. 487 – 491;,
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Synthetic Route of 18392-81-9, 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. 18392-81-9, name is 5,6-Dibromobenzo[c][1,2,5]thiadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Take 100mL reaction tube,5,6-dibromobenzothiadiazole (2.94 g, 10 mmol) was added,2-dodecylthiophene (2.77 g, 11 mmol),Potassium carbonate (1.66 g, 12 mmol),Trimethylacetic acid (306 mg, 3 mmol),5% of the catalyst palladium acetate,Nitrogen vacuum drum,30 mL of anhydrous N, N-dimethylacetamide was injected with a syringe,Stir at room temperature for 1 minute to make it fully dissolved,110 C for 4 hours.After completion of the reaction, the mixture was extracted with ethyl acetate,Add more saturated salt water layer is more obvious.Dried over anhydrous sodium sulfate,The solvent was removed under reduced pressure to give the crude product,Column chromatography,Petroleum ether / dichloromethane (8: 1).To give the product 1a (2.79 g, 60%),Light yellow oily liquid.

The synthetic route of 5,6-Dibromobenzo[c][1,2,5]thiadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Fu, Nina; Huang, Wei; Shi, Xin; Zhao, Baomin; Liu, Shuli; Wang, Lianhui; (15 pag.)CN106008558; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, 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 3972-64-3, Application In Synthesis of 1-Bromo-3-(tert-butyl)benzene

To a solution of 1 (15mg, 0.079mmol), 2 (33mg, 0.158mmol) and Cs2CO3 (128mg, 0.395mmol) in DMF (lmL) were added 2 mg of Pd(dba)2 and 2 mg of Xantphos. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 120 ¡ãC for 6h. LCMS showed the SM was consumed completely. Then the reaction mixture was diluted with EA (10mL) and washed with brine (2mL) twice. The organic solution was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified by p-TLC to give the desired compound Compound 221 (3mg, yield: 12percent). LCMS: m/z, 323.2 (M+H)+; 1HNMR (CDCl3, 400MHz): delta 8.62(d, J=4.8, 1H), 7.68~7.73(m, 1H), 7.52(d, J=7.6, 1H), 7.30(t, J=6.4, 1H), 7.20(t, J=8.0, 1H), 6.79(d, J=7.2, 1H), 6.58(s, 1H), 6.41(d, J=5.6, 1H), 3.92(s, 1H), 3.86(s, 1H), 3.56~3.60(m, 2H), 2.61~2.74(m, 1H), 2.47~2.56(m, 1H), 1.32(s,9H).

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Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 33070-32-5

Example 35A ethyl 4-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)butanoate To a solution of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (9.9 g, 41.8 mmol) in tetrahydrofuran (40 mL) was added 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.343 g, 0.835 mmol) and palladium(II) acetate (0.094 g, 0.418 mmol). A 0.5 M solution of 4-ethoxy-4-oxobutylzinc bromide in tetrahydrofuran (100 mL, 50.1 mmol) was added to the reaction mixture at ambient temperature under nitrogen over 15 minutes. A slight exotherm from 22 C. to 42 C. was noted. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and 1 N HCl solution. The organic fraction was separated, washed by brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using a 220 g silica gel cartridge eluted with 0-10% tert-butyl methyl ether/heptanes to give the title compound (8.96 g, 79% yield). 1H NMR (400 MHz, CDCl3) delta ppm 1.28 (t, J=7.1 Hz, 3H), 1.95 (p, J=7.5 Hz, 2H), 2.33 (t, J=7.4 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 6.84-6.95 (m, 2H), 6.98 (d, J=8.1 Hz, 1H).

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 33070-32-5.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
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These common heterocyclic compound, 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, 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. Quality Control of 2-(Aminomethyl)-4-bromoaniline

To dichloromethane (DCM) (3.5 L), 5-bromo-2-amino-benzylamine (137g, 0.5 mol) and triethylamine (TEA) (250 mL, 1.75 mol) were added at O0C on stirring. Then benzoyl chloride (55 mL, 0.45 mol) in DCM (500 mL) was added on stirring at such a rate to keep the temperature at 0-50C. The mixture was stirred for 3 hours at r.t.. Water (1 L) was added and the organic phase was separated, washed with water and dried. The solvent was evaporated and SOCl2 (100 mL) was added to the residue (147.5 g) suspended in toluene (1.5 L). The obtained suspension was heated at reflux for 72 hours. On cooling a precipitate was formed, it was filtered, washed with toluene and suspended in aqueous ammonia, the suspension was extracted with AcOEt. The combined organic phases were washed with water, dried and concentrated to afford the dihydroquinazoline derivative, as a light brown solid (93.8 g., 64% yield). The dihydroquinazoline was dissolved in DCM (2 L) and MnO2 (56.28 g) was added on stirring. The resulting suspension was stirred at r.t. for 18 hours. The suspension was filtered on celite, the cake was washed with DCM and the combined filtrate and washings were concentrated to afford the titled product as an amorphous solid, 85.54 g (60 % overall yield; 95% oxidation yield). Ci4H9BrN2; MW: 285.15; MS m/z: 286 (M+ 1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, IH), 8.17 (dd, IH), 8.49-8.56(m, 3H), 9.70(s, IH).

The synthetic route of 2-(Aminomethyl)-4-bromoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; WO2009/152868; (2009); A1;,
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Electric Literature of 876-53-9,Some common heterocyclic compound, 876-53-9, name is 1,3-Dibromoadamantane, molecular formula is C10H14Br2, 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.

In a 250 ml round bottom flask, 1,3-dibromoadamantane (15 mmol), cuprous oxide (40 mmol), and DMAC (20 ml) were refluxed for 48 hours under an argon atmosphere.The obtained intermediate was cooled to room temperature, added to water, then filtered through a pad of Celite, and the filtrate was extracted with dichloromethane.The organic phase was then washed with water and the organic phase was dried over anhydrous magnesium sulfate.After filtering and evaporating the organic phase, the crude product was purified by silica gel column chromatography.The intermediate product H14-1 was obtained.

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-Dibromoadamantane, its application will become more common.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Dai Wenpeng; Gao Wei; Niu Jinghua; Zhang Lei; Lu Yan; Deng Dongyang; (40 pag.)CN110156756; (2019); A;,
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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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Product Details of 54962-75-3

A solution of l-allyl-4-methylpiperazine (2.12 g, 14.0 mmol) and 9-BBN (0.5 M in THF, 1.7 g, 28 mL, 14.0 mmol) was EPO heated at reflux for 3 h and then cooled to RT. The solution was added to a mixture of 3-bromo-5- (trifluoromethyl)aniline (3.Oo g, 12.5 ittmol) , potassium carbonate (8.64 g, 62.5 mmol) , PdCl2(PPh3J2-CH2Cl2 adduct (0.457 g, 0.6 mmol) , DMF (30 mL) and water(2 mL) . The mixtre was heated to 75C for 24. The mixture was concentrated, triturated with dichloromethane, and filtered. The filtrate was concentrated and the residue was purified via column chromatography on silica gel (gradient elution with 0-20% methanol-dichloromethane) to afford 3- (3- (4-methylpiperazin- 1-yl)propyl) -5- (trifluoromethyl)benzenamine as a brown oil. MS m/z = 302 [M+H]+. CaIc’d for C15H22F3N3: 301.

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
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Electric Literature of 1435-52-5, 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 1,4-dibromo-2-fluorobenzene (6.86 g, 27 mmol), ethanediol (35 mL), N-methylpyrrolidone (35 mL) and potassium tert-butoxide (11.2 g, 95 mmol) was stirred at 100 C overnight under N2. After the mixture was cooled to room temperature, water (15 mL) was added slowly within 30 min. Then the mixture was filtered, and the filter cake was washed by ethanediol. To the filtrate was added water and the mixture was stirred for 30 min. The resulting solution was then cooled to 15 C, and let stay for 1 h. The precipitate was filtered, washed by water, and dried to give the title compound (4.70 g, 59 %). 1H NMR (CDCl3): delta 7.40 (1H, d, J = 8.4 Hz), 7.05 (1H, d, J = 2.4 Hz), 7.02-6.70 (1H, m), 4.14 (2H, t, J = 4.4 Hz), 4.02-3.98 (2H, m), 2.13 (1H, t, J = 6.4 Hz)

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

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
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