Tag: M.W=300-400

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. 3344-70-5, name is 1,12-Dibromododecane, A new synthetic method of this compound is introduced below., Recommanded Product: 1,12-Dibromododecane

General procedure: Finelyground KOH (2.24 g, 40 mmol) was added to a solution of3,5-dimethylpyrazole (1.92 g, 20 mmol) in DMSO (10 ml).The suspension was thoroughly stirred for 30 min at 80°.Then a solution of 1,4-dibromobutane (2.16 g, 1.21 ml,10 mmol) in DMSO (10 ml) was added dropwise over30 min, while cooling the reaction mixture with water.After finishing the addition of dibrom derivative, stirringand heating at 80° were continued for additional 4 h, andthe reaction mixture was then poured into water (200 ml).The white precipitate that formed was filtered off, washedwith water, and dried.

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; Zatonskaya, Lina V.; Schepetkin, Igor A.; Petrenko, Tatiana V.; Ogorodnikov, Vladimir D.; Khlebnikov, Andrei I.; Potapov, Andrei S.; Chemistry of Heterocyclic Compounds; vol. 52; 6; (2016); p. 388 – 401; Khim. Geterotsikl. Soedin.; vol. 52; 6; (2016); p. 388 – 401,14;,
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Electric Literature of 2789-89-1, A common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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 solution of di(4-bromophenyl)acetylene (719 mg, 2.14 mmol, 1 equiv) in dry THF (60 mL) was added the fresh solution (Ca. 0.4 mol/L) of (4-dodecylphenyl)magnesium bromide (20 mL, 8.57 mmol, 4 equiv) in a flame-dried apparatus. PdCI2(dppf) (138 mg,0.17 mmol, 8 mol%) was then added and the reaction mixture was stirred at reflux under argon overnight. The solution was then cooled down to room temperature. The obtained white precipitate was filtered and washed with methanol and petroleum ether. 044 was obtained as an off-white solid (1.1672 mg, 82%).

The synthetic route of 2789-89-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF BIRMINGHAM; BARANOFF, Etienne David; HERBAUT, Antoine Joel Maurice; (37 pag.)WO2016/193748; (2016); A1;,
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Electric Literature of 626-39-1, These common heterocyclic compound, 626-39-1, name is 1,3,5-Tribromobenzene, 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.

[0372] 1,3,5-Tribromo-benzene (31.4 g, 100 mmol) was dissolved under argon in a flame dried three-neck flask in 1000 mL diethylether and the solution was cooled to -72C. A solution of 62 mL r°BuLi (1.6 M in hexane, 100 mmol) was added to the resulting suspension in such a fashion that temperature did not rise above -7O0C. The mixture was stirred for 30 min at -750C and the reaction was monitored by HPLC. A solution of 10.4 g (100 mmol) 3-cyanopyridine in 100 mL diethylether was added in such a fashion that temperature did not rise above -710C. The mixture was stirred at -75C for 60 min and the reaction was monitored by HPLC. The cooling bath was removed and warmed to -250C. 2 N HCl (250 mL) was added and the mixture was stirred for 20 min at room temperature. The mixture was made alkaline by addition of 1 N NaOH. The product was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4. The product was purified by chromatography (700 g silica agel, CH2Cl2, then CH2Cl2 / ethyl acetate 1:1, UV) to yield 27.7 g (81 %) of (3,5-dibromo-rhohenyl)-pyridin-3-yl-methanone.

The synthetic route of 626-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
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955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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. Quality Control of 4-(4-Bromophenyl)dibenzo[b,d]furan

[Example-of-Synthesis 1 (Synthesis of Compound H1) ]; Under an argon gas flow, 6.5 g of Intermediate 5, 9.5 g of Intermediate 12, 2.6 g of t-butoxy sodium (manufactured by Hiroshima Wako Co., Ltd.), 92 mg of tris (dibenzylideneacetone) dipalladium(0) (manufactured by SIGMA-ALDRICH Corn.), 42 mg of tri-tert-butylphosphine and 100 ml of dehydrated toluene were placed and the reaction was allowed to proceed at 80°C for 8 hours. The resultant solution was cooled down, added with 500 ml of water and filtered through sellite. The resultant filtrate was extracted with toluene, and the extract was dried over dehydrated magnesium sulfate. The dried substance was condensed under reduced pressure and the coarse product was subjected to column purification. The purified substance was re-crystallized with a use of toluene and after the resultant crystal was taken by filtration, the crystal was dried and as a result, 8.1 g of a pale yellow powder was obtained. The pale yellow powder was identified as Compound H1 from the result in accordance with the FD-MS analysis.

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2295421; (2011); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 61921-39-9 as follows. Quality Control of 4-Bromotetraphene

52 ml (130 mmol) of n-butyllithium (2.5 M in n-hexane) are added dropwise with vigorous stirring to a suspension of 30.7 g (100 mmol) of 4-bromo-benz[a]anthracene (I) in 1000 ml of THF at -78 C., and the mixture is stirred for a further 2 h. 16.7 ml (150 mmol) of trimethyl borate are added in one portion to the red solution with vigorous stirring, the mixture is stirred at -78 C. for a further 30 min., then warmed to room temperature over the course of 3 h, 300 ml of water are added, and the mixture is stirred for 30 min. The organic phase is separated off and evaporated to dryness in vacuo. The solid is taken up in 100 ml of n-hexane, filtered off with suction, washed once with 100 ml of n-hexane and dried in vacuo. Yield: 23.7 g (87.0 mmol), 87.0%, purity about 90.0% (NMR) of boronic acid, with varying amounts of boronic anhydride and borinic acid. The boronic acid can be used in this form without further purification.

According to the analysis of related databases, 61921-39-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent GmbH; Anemian, Remi Manouk; Ludemann, Aurelie; Eberle, Thomas; Hoeger, Sigurd; Reis, Eva Maria; Bobbe, Vanessa; US8906893; (2014); B2;,
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Related Products of 2789-89-1, 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. 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A small molecule luminescent material (P37) based on 1,2-diphenylacetylene as the acceptor unit,The specific steps are:Under nitrogen protection,To a three-necked flask was added 100 ml of toluene,1 g of intermediate 1 (2.99 mmol),2.14 g of 9-phenyl-3-carbazole boronic acid (7.45 mmol, 2.5 equ)Under stirring, 3.47 g of sodium tert-butyl alcohol was added,Then add 230 mg of palladium acetate,0.5 mL of tri-tert-butylphosphine,90 & lt; 0 & gt; C overnight.Cooling, extraction of organic phase with methylene chloride, spin dry,Column. To give 1.48 g of product as a yellow solid in 75% yield.

The synthetic route of 1,2-Bis(4-bromophenyl)ethyne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China University of Technology; Su Shijian; He Zuozheng; Ma Wuguang; Peng Junbiao; Cao Yong; (30 pag.)CN106242976; (2016); A;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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 52997-43-0, Formula: C16H33Br

The aqueous NaOH solution (13.5 ml, 6 M) was placed in a reaction flask,Ventilation (nitrogen) three times,A solution of p-bromophenethyl mercaptan (9.77 g, 45 mmol) was added dropwise under nitrogen,After dripping,The phase transfer catalyst was added tetrabutylammonium iodide (catalyst amount, 1.99 g).Ten minutes later, 61 ml of tetrahydrofuran was added,To be uniform,Ethyl 2-hexyl decane (16.50 g, 54 mmol) was added dropwise over 10 min.The temperature was then raised to 45 C,The reaction was stirred overnight under vigorous stirring.Reaction is completed,The reaction solution was poured into dilute hydrochloric acid (1 M)Extracted with dichloromethane,Dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure,The column was crystallized from 16.3 g of a colorless transparent liquid in 85% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Bromomethyl)pentadecane, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Institute of Printing; Wang, Wenguang; Yang, Mingcong; Pu, Jialing; (29 pag.)CN104961665; (2017); B;,
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. 3344-70-5, name is 1,12-Dibromododecane, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C12H24Br2

General procedure: The new inhibitors (3-22; Fig. 3) were prepared via standard synthetic strategy [24] and [25]. The solution of isoquinoline (1.6 g, 12.4 mmol) and corresponding alkylating agent (5.6 mmol) in DMF (10 ml) was stirred at 70 °C. The reaction mixture remained at the room temperature. It was portioned with acetone (50 ml) and cooled in refrigerator (5 °C) overnight. The crystalline or amorphous crude product was collected by filtration, washed with acetone (3 .x. 20 ml) and recrystallized from MeCN. NMR, ESI-MS and elemental analysis determined the entity and purity of all prepared compounds.

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 3344-70-5.

Reference:
Article; Musilek, Kamil; Komloova, Marketa; Holas, Ondrej; Hrabinova, Martina; Pohanka, Miroslav; Dohnal, Vlastimil; Nachon, Florian; Dolezal, Martin; Kuca, Kamil; European Journal of Medicinal Chemistry; vol. 46; 2; (2011); p. 811 – 818;,
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Synthetic Route of 4101-68-2, 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. 4101-68-2, name is 1,10-Dibromodecan, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred suspension of salicyaldehyde (2 mL, 20 mmol) and potassiumcarbonate (5.52 g, 40 mmol) in DMF (100 mL) was added 1,10-dibromodecane (10.8mL, 48 mmol). The mixture was stirred at 80 C for 3 h, and the solvent was evaporated under reducedpressure. The resulting residue was triturated with ether (1000 mL), and theorganic phase was washed with dilute sodium hydroxide solution, water, brine,and dried over sodium sulfate. After evaporation of the solvent, the residuewas purified by column chromatography (petroleum/ethyl acetate, 20:1), toafford compound 2 (2.45 g, 36%) as an oil. 1H NMR(300 M,CDCl3): d 1.31-1.46 (m, 12 H), 1.82-1.87 (p, 4 H), 3.41 (t, J =6.90 Hz, 2 H), 4.07 (t, J = 6.30 Hz, 2 H), 6.99 (m, 2 H), 7.52 (m, 1 H), 7.81(m, 1 H), 10.50 (s, 1 H). MS (EI) (m/e): 340 (M-H+). Anal. Calcd forC17H25BrO2: C, 59.83%; H, 7.38%; O, 9.38%.Found: C, 59.32%; H, 7.98%.

The chemical industry reduces the impact on the environment during synthesis 1,10-Dibromodecan. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Hui; Li, Zhan-Ting; Chinese Chemical Letters; vol. 25; 5; (2014); p. 659 – 662;,
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Synthetic Route of 615-54-3, The chemical industry reduces the impact on the environment during synthesis 615-54-3, name is 1,2,4-Tribromobenzene, I believe this compound will play a more active role in future production and life.

Step 1: Into a 100-nt 3-necked round-bottom flask, was placed a mixture of 1,2.4- tribromobenzene (5,20 g, 16.52 mmol, 1.00 equiv) and 2-methylfuran (4.18 g. 50.91 mmol,3.00 equiv) in toluene (30 mL) with stirring at -30 C, followed by the drop-wise addition of n-BuLi (7.48 mL, 1.10 equiv). The resulting mixture was stirred for 30 mm at -30 C then it was quenched by the addition of 50 mL of 1120, cooled to RT and extracted with 3 x 50 mL of ethyl acetate. The organic layer was washed with 200 mL of 1120, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gelcolumn chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 2.10 g (54%) of a mixture of (+)-4-bromo- i-methyl-li -oxatricyclo [6.2.1. 02?7jundeca-2,4,6,9- tetraene and (+)-5-bromo- i-methyl-il -oxatricyclo[6. 2.1.0271 undeca-2,4,6,9-tetraene as a light yellow solid. Step 2: Into a l00-mL 3-necked round-bottom flask, was placed a solution of (+)-4- bromo- 1-methyl-il -oxatricyclo [6.2.1.0271 undeca-2,4,6,9-tetraene and (+)-5-bromo- 1-methyl- l1-oxatricyclo[6.2.1.02?7jundeca-2,4,6,9-tetraene (2.10 g, 8.86 mmol, 1.00 equiv) in chloroform (30 mL) with stirring at rt, followed by the slow addition of a solution ofbis(pyridin-2-yl)-1,2,4,5-tetrazine (2.40 g, 10.16 mmol, 1.10 equiv) in chloroform (20 mL). The resulting mixture was stirred for 1 h at 50 C to deliver the mixture of corresponding isobenzofurans intermediate (50 mL) as a red solution. To this solution into a 100-mL 3- necked round-bottom flask at 0 C was added a solution of [5-(methoxycarbonyl)-2- (trimethylsilyl)phenyl](phenyl)iodanium trifluoromethanesulfonate (5.60 g, 9.99 mmol, 1.00equiv) in dichioromethane (40 mL), followed by TBAF (5.23 g, 20.00 mmol, 2.00 equiv). The resulting mixture was stirred for 30 mm at 0 C then it was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 900 mg (26%) of (+)-methyl 12-bromo-8-methyl-15- oxatetracyclo [6,6,1,027, 4i pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl11 -bromo-8-methyl- 1 5-oxatetracyclo[6. 6.1. 02?.O9?14jpentadeca-2(7),3,5,9,1 1,1 3-hexaene-4- carboxylate, (+)-methyl 1 2-bromo- 1-methyl-i 5-oxatetracyclo-[6. 6,i,02?. 09?14jpentadeca- 2(7),3,5,9. 11,1 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5- oxatetracyclo [6.6. i .027. 14j pentadeca-2(7),3 ,5 ,9, ii, i 3 -hexaene-4-carboxylate as a light yellow solid. Step 3: Into a 50-mL round-bottom flask, was placed a mixture of (+)-methyl i2- bromo-8-methyl-1 5-oxatetracyclo[6. 6.1.02,7. 09?4jpentadeca-2(7),3,5,9, ii, i 3-hexaene-4- carboxylate (+)-methyl ii -bromo-8-methyl- i 5-oxatetracyclo[6. 6. i .02,7. ue 14j pentadeca2(7),3,5 ,9. 11,1 3-hexaene-4-carboxylate, (+)-methyl 1 2-bromo- 1-methyl- 15- oxatetracyclo[6.6. 1.027.09141 -pentadeca-2(7),3.5.9,1 1, i 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5-oxatetracyclo[6. 6. i .02,7. 09?4jpentadeca-2(7),3,5,9, ii ,13- hexaene-4-carboxylate (500.0 mg, 1.45 mmol, 1.00 equiv), dioxane/H20 (5/0.5 mL), (4- fluorophenyl)boronic acid (665.0 mg, 4.75 mmol, 1.50 equiv), sodium carbonate (46i.0 mg, 4.35 mmol, 3.00 equiv) and Pd(dppf)Cl2 (53.0 mg, 0.07 mmol, 0.05 equiv) with stirring under N2. The resulting mixture was stirred for 3 h at 90 C then it was cooled to RT andconcentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (iS) to afford 4 i 0.0 mg (79%) of a mixture of (+)-methyl 1 2-(4-fluorophenyl)-8-methyl- i 5-oxatetracyclo- [6.6. i .02,7. ?4jpentadeca- 2(7),3,5 ,9. ii, 1 3-hexaene-4-carboxylate, (+)-methyl ii -(4-fluorophenyl)-8-methyl- 15-oxatetracyclo [6.6.1.02,7. ue 14j pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl 12-(4-fluorophenyl)-1 -methyl-i 5-oxatetracyclo[6. 6.1. 02?7.09?4j-pentadeca-2(7),3,5,9, 11,13- hexaene-4-carboxylate and (+)-methyl ii -(4-fluorophenyl)- 1-methyl-i 5- oxatetracyclo [6.6.1.027. 14j pentadeca-2(7),3 ,5 ,9, 11,13 -hexaene-4-carboxylate as a lightyellow solid..

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, 1,2,4-Tribromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; ZANCANELLA, Manuel; YU, Chul; SETTI, Lina; SHAM, Hing; XU, Qing; YEE, Calvin; YU, Ming; (402 pag.)WO2016/201052; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary