Tag: M.W=100-200

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. 626-88-0, name is 1-Bromo-4-methylpentane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-methylpentane

General procedure: A Grignard suspension of 1-bromo-4-methylpentane in THF (50 mL) was prepared from the bromide (1.64 g, 9.94 mmol) and Mg (0.29 g, 11.92 mmol) in the usual manner. The suspension was cooled (-50 C) and Cu(I) bromide (0.712 g, 4.97 mmol) was added to it. The mixture was stirred for 15 min. To the resultant black suspension at -50 C was added compound 8a (1.5 g, 3.31 mmol) in THF (40 mL). The mixture was stirred at the same temperature for 1 h and then overnight at room temperature. The reaction was quenched by the addition of aqueous saturated NH4Cl (10 mL) and extracted with EtOAc. The organic layer was washed with 5% aqueous HCl, water, brine, and then dried over Na2SO4. Solvent removal under reduced pressure and column chromatography of the residue (silica gel, 0-10% EtOAc in hexane) afforded pure 9a (1.24 g, yield 70%) as a colorless liquid.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dubey, Akhil Kumar; Chattopadhyay, Angshuman; Tetrahedron Asymmetry; vol. 22; 14-15; (2011); p. 1516 – 1521;,
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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. 2550-36-9, name is (Bromomethyl)cyclohexane, A new synthetic method of this compound is introduced below., Recommanded Product: (Bromomethyl)cyclohexane

Example 4A 3-(Cyclohexylmethoxy)pyridine-2-amine At RT, 96 g of sodium hydroxide 45% strength in water (1081 mmol, 1 equivalent) were initially charged in 1170 ml of methanol, 119 g of 2-amino-3-hydroxypyridine (1080 mmol, 1 equivalent) were added and the mixture was stirred at RT for 10 min. The reaction mixture was concentrated under reduced pressure, the residue was taken up in 2900 ml of DMSO and 101 g of cyclohexylmethyl bromide (1135 mmol, 1.05 equivalents) were added. After 16 h at RT, the reaction mixture was added slowly to 6 l of water and the aqueous solution was extracted twice with in each case 21 of ethyl acetate. The combined organic phases were washed with in each case 1 l of saturated aqueous sodium bicarbonate solution and water, dried, filtered and concentrated. The residue was triturated with 500 ml of n-pentane, filtered and dried under reduced pressure. This gave 130 g (58% of theory) of the title compound. LC-MS (Method 3): Rt=1.41 min MS (ESpos): m/z=207.1 (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; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; FOLLMANN, Markus; HARTUNG, Ingo; BUCHGRABER, Philipp; JAUTELAT, Rolf; HAssFELD, Jorma; LINDNER, Niels; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER, Eva-Maria; KNORR, Andreas; US2014/128372; (2014); A1;,
Bromide – Wikipedia,
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Electric Literature of 1073-39-8, These common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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.

Step 2 N-(bicyclo[4.2.0]octa-1(6),2,4-trienyl-3-yl)-N’-(tert-butoxycarbonyl-hydrazino)-tert-butyl-carbonate; 3-Bromo-bicyclo[4.2.0]octa-1(6),2,4-triene 5b (13.5 g,73.8 mmol) was dissolved in 100 mL of dry tetrahydrofuran. The mixture was cooled to -78 C in a dry ice-ethanol bath and then n-butyllithium (66 mL, 165 mmol) was added. A solution of di-tert-butyl azodicarboxylate (20.1 g, 87.4 mmol) in 80 mL of dry tetrahydrofuran was added dropwise under stirring at the same temperature. Upon completion of the addition, the dry ice-ethanol bath was removed and the mixture was warmed up to room temperature and stirred overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction was quenched with 100 mL of water and the layers were separated. The aqueous layer was extracted with ethyl acetate (100 mLx2). The combined organic extracts were washed with saturated brine (150 mL¡Á1), dried over anhydrous sodium sulfate and filtered to remove the drying agent. The filtrate was purified by silica gel column chromatography to obtain the title compound N-(bicyclo[4.2.0]octa-1(6),2,4-trienyl-3-yl)-N’-(tert-butoxycarbonyl-hydrazino)-tert-butyl-carbonate 5c (4.07 g, 16.5%) as a yellow oil.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2236500; (2010); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 10269-01-9, name is (3-Bromophenyl)methanamine, 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 10269-01-9, Quality Control of (3-Bromophenyl)methanamine

A mixture of (3-bromophenyl)methanamine (5.4 g, 29 mmol), AcCl (2.7 g, 29 mmol) and Et3N (5.9 g, 58 mmol) in DCM (100 mL) was stirred at rt for 3 h, then it was quenched with water (20 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were concentrated in vacuo. The residue was recrystallized from hexanes/EtOAc (10/1, 55 mL) to afford the title compound. 1H NMR (CDC13, 400 MHz): delta 7.40-7.36 (m, 2H), 7.20- 7.15 (m, 2H), 6.01 (br s, 1H), 4.37 (d, / = 6.0 Hz, 2H), 2.01 (s, 3H).

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); 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. 103-64-0, name is (2-Bromovinyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

At room temperature,To the appropriate amount of the organic solvent DMF was added 100 mmol of the compound of the above formula (I)220 mmol of the compound of formula (II)6 mmol of catalyst (2.4 mmol of Pd (TFA) 2 with 3.6 mmol of Cu (acac) 2)50 mmol of 1-ethyl ethyl ether-3-methylimidazolebis (trifluoromethanesulfonyl) imide and 300 mmol of triisopropanolamine,Then heated to 80 C,And the reaction was stirred at that temperature for 6 hours; After the reaction,The resulting mixture was filtered while hot,To obtain a filtrate;To the filtrate was added a 10% hydrochloric acid solution with a mass percentage of 10%Adjust the pH to neutral;Then ethyl acetate,Oscillation extraction 2-3 times,Combined organic phase,Dried over anhydrous magnesium sulfate,Then concentrated under reduced pressure,The resulting residue was subjected to 200-300 mesh silica gel column chromatography,The petroleum ether-n-butanol mixture was used as the eluent,Wherein the volume ratio of petroleum ether to n-butanol is 10: 1,Thereby obtaining a compound of the above formula (III)The yield was 97.4%.

According to the analysis of related databases, 103-64-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University; Xia Yunqiu; Zhou Yingbin; Wang Yanxin; Zhong Weizhen; Guo Shenbo; (9 pag.)CN104803912; (2017); B;,
Bromide – Wikipedia,
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Application of 766-81-4, A common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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.

General procedure: In a glove box filled with nitrogen, to an oven-dried 5 mL pressure tube equipped with a stir bar were added CuI (0.015 mmol, 2.9 mg, 0.050 equiv), 4,4′-di-tert-butyl-2,2′-dipyridine (2.0 mg, 0.0075 mmol, 0.025 equiv), azide compounds (0.36 mmol, 1.2 equiv), terminal alkynes (0.30 mmol, 1.0 equiv), (CF3CF2CO)2O (0.39 mmol, 120.9 mg, 1.3 equiv), Et3N (0.45 mmol, 45.5 mg, 1.5 equiv) and THF/n-C6H14 (1:1, 1.0 mL). The tube was sealed with Teflon screw cap and the solution was stirred at 50 C for 15 h. The reaction mixture was cooled to room temperature and was filtered through a layer of Celite, eluted with dichloromethane. The solvent was removed by rotary evaporation and the resulting product was purified by column chromatography on silica gel with n-pentane/ dichloromethane.

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Bo; Wu, Wei; Weng, Zhiqiang; Tetrahedron; vol. 75; 19; (2019); p. 2843 – 2847;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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. category: bromides-buliding-blocks

Preparation 3 1-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde Imidazole-4-carboxaldehyde (4.8 g, 50 mmol) was added portionwise to a suspension of sodium hydride (2.20 g, 60% dispersion in mineral oil, 55 mmol) in tetrahydrofuran (150 ml), and the mixture was then stirred at room temperature for 1 hour. 2-Cyclohexylethyl bromide (8.6 ml, 55 mmol) was added, and the mixture was heated under reflux for 18 hours. The cooled mixture was evaporated under reduced pressure and the residue was partitioned between water (500 ml) and dichloromethane (500 ml). The layers were separated, and the organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4) to afford the title compound, 1.78 g. 1H-NMR (CDCl3, 400 MHz) delta: 0.98 (m, 2H), 1.20 (m, 4H), 1.68 (m, 7H), 4.00 (t, 2H), 7.4 (s, 1H), 7.60 (s, 1H), 9.80 (s, 1H). LRMS: m/z (TSP+) 207.2 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1647-26-3, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2003/199522; (2003); A1;,
Bromide – Wikipedia,
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Synthetic Route of 4117-09-3, These common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, 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.

Grignard reagent hept-6-en-1-ylmagnesium bromide was prepared by suspending magnesium granules (0.22g, 9.05mmol) in anhydrous tetrahydrofuran (20mL) and subsequently adding 7-bromo-1-heptene (1.63g, 9.19mmol) dropwise. The mixture was refluxed for 30min. In a separate flask, copper(I) iodide (1.72g, 9.03mmol) was suspended in anhydrous tetrahydrofuran (10mL) and cooled to-78C in an isopropyl alcohol-dry ice bath. Methyllithium solution (1.6M in diethyl ether, 5.65mL, 9.04mmol) was added very slowly via syringe. The resultant mixture was stirred at-78C for 1h and then slowly allowed to warm to 0C, whereupon a brownish suspension formed, which was immediately cooled to-78C. After that, the aforementioned solution of Grignard reagent in tetrahydrofuran was added via syringe. The mixture thus obtained was stirred at-78C for 1h and then allowed to warm to 0C, whereupon a purple colouration appeared. The mixture was then cooled again to-78C and a solution of 1 (1.47g, 4.51mmol) in tetrahydrofuran (20mL) was added via syringe. That mixture was allowed to stir at-78C for 1h and at room temperature for 2h, and the reaction was quenched by adding saturated aqueous ammonium chloride (15mL). After addition of diethyl ether (50mL), two layers and a brown insoluble formed which was filtered off. The organic phase was separated and the royal blue aqueous phase was extracted with diethyl ether. The combined organic fractions were washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. Flash column chromatography of the residual brown oil with n-hexane-diethyl ether (95:5) yielded the crude ester mixture (0.56g, 42%). A 0.23g portion was separated from the by-product 3 by passing over a 10g SPE cartridge. Step gradient elution from acetonitrile-water (9:1) to pure acetonitrile yielded pure ester 2 as a white solid (0.20g, 96%) after concentration under reduced pressure. TLC (n-hexane-diethyl ether 9:1): Rf 0.43. RP-TLC (acetonitrile): Rf 0.22. 1H NMR (400MHz, CDCl3): delta 5.80 (1H, ddt, J=16.9, 10.1, 6.6Hz), 5.00-4.89 (2H, m), 3.65 (3H, s), 2.28 (2H, t, J=7.4Hz), 2.05-1.99 (2H, m), 1.60 (2H, qui, J=7.3Hz), 1.38-1.20 (24H, m). 13C NMR (100MHz, CDCl3): delta 174.4, 139.3, 114.1, 51.5, 34.2, 33.9, 29.7 (3), 29.6, 29.5, 29.3, 29.2, 29.0, 25.0. GC: tR 16.6min. EIMS (70eV): m/z (%) 296 (1), 264 (51), 222 (28), 180 (19), 111 (19), 97 (45), 87 (59), 74 (83), 55 (100), 41 (58).

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

Reference:
Article; Huber, Thimo; Firlbeck, Doris; Riepl, Herbert M.; Journal of Organometallic Chemistry; vol. 744; (2013); p. 144 – 148;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Intermediate 20-1Preparation of N-(3-bromo-2-methylphenyl)-1H-indazol-3-amine Step 1 A mixture of 3-bromo-2-methylaniline (1.66 mL, 13.4 mmol), 2-fluorobenzoic acid (1.883 g, 13.4 mmol), and HOAT (2.74 g, 20.2 mmol) in EtOAc (60 mL) was treated with DIEA (4.7 mL, 26.9 mmol) and EDC (5.15 g, 26.9 mmol) and the mixture was stirred at rt. After 19 h, the mixture was diluted with EtOAc and washed with water, 1 M hydrochloric acid (twice), NaHCO3 (aq) (twice) and brine, dried and concentrated to provide N-(3-bromo-2-methylphenyl)-2-fluorobenzamide as tan fluffy needles (4.11 g, 99%). 1H NMR (400 MHz, chloroform-d) delta 8.34-8.50 (1 H, m), 8.20 (1H, td, J=7.9, 1.8 Hz), 7.96 (1H, d, J=8.1 Hz), 7.50-7.59 (1H, m), 7.44 (1H, dd, J=8.0, 0.8 Hz), 7.30-7.37 (1H, m), 7.21 (1H, dd, J=12.8, 7.9 Hz), 7.12 (1H, t, J=8.0 Hz), 2.45 (3H, s). Mass spectrum m/z 308, 310 (M+H)+.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, 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. name: 1-Bromo-3,5-dimethylbenzene

Under an argon atmosphere, a solution of magnesium (25 g, 0.95 equivalent) and a small amount of iodine in THF (250 mL) was stirred at room temperature for 1 hr. 5-Bromo-m-xylene (200 g, 1.08 moL) was added at 48C, and the mixture was stirred at 5C for 1 hr. Diethyl phosphite (78.3 g, 0.52 equivalent) was added at 5C, and the mixture was stirred at 5C for 2 hrs. Water (200 mL) was added at 3C, and toluene (200 mL) and 6M-HCl (160 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed successively with water (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered by gravity. The filtrate was concentrated under reduced pressure and the residue was recrystallized from diisopropyl ether-heptane to give the title compound (43.3 g, white crystals). yield 33.3%.

The synthetic route of 1-Bromo-3,5-dimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1452537; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary