Tag: M.W=200-300

Synthetic Route of 3972-64-3, A common heterocyclic compound, 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, molecular formula is C10H13Br, 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.

2-(3-(Tert-butyl)phenyl)ethanol To a vial was added the 1-bromo-3-(tert-butyl)benzene (0.107 g, 0.502 mmol) and dry THF. The reaction was then cooled to -78¡ã C. and the BuLi (0.221 mL, 0.552 mmol) (2.5 M in hexanes) was added dropwise and the reaction stirred for 30 min at -78¡ã C. and then ethylene oxide (0.502 mL, 1.255 mmol) (2.5-3.3M solution in THF) was added dropwise and the reaction stirred for 10 minutes at -78¡ã C. then warmed to rt and stirred for 1 h. The reaction was then quenched with 1.0 M HCl (2 mL) and extracted with EtOAc (3*5 mL). The EtOAc layer was combined, concentrated and purified by reverse-phase MPLC (10-100percent MeCN:water) to produce pure 2-(3-(tert-butyl)phenyl)ethanol (0.035 g, 0.196 mmol, 39percent yield). 1H NMR (400 MHz, CDCl3): delta 7.31-7.27 (m, 3H), 7.10-7.07 (m, 1H), 3.90 (t, J=6.6 Hz, 2H), 2.91 (t, J=6.5 Hz, 2H), 1.52 (br s, 1H), 1.36 (s, 9H).

The synthetic route of 3972-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF ROCHESTER; UNIVERSITY OF KANSAS; Dunman, Paul M.; Krysan, Damian J.; Flaherty, Daniel P.; US2015/238473; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 6274-57-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6274-57-3 name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1195-33-1, 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 1195-33-1 as follows.

General procedure: A sealable reaction tube equipped with a magnetic stirrer bar was charged with 2-(allyloxy)benzaldehyde (0.2mmol), benzenesulfinic acid (3.0 equiv.), Na2-Eosin Y (4 mol%), K2S2O8 (3.0 equiv.), DMF_H2O=1:1 (2 ml), 8W blue. The reaction vessel was carried out room temperature. After completion, it was diluted with ethylacetate, washed with water. After the solvent was removed under reduced pressure, the residue was purified bycolumn chromatography on silica gel to afford the corresponding product.

According to the analysis of related databases, 1195-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, De-Mao; Han, Qing-Qing; Li, Guang-Hui; Sun, Yuan-Yuan; Wang, Zu-Li; Xu, Xin-Ming; Yu, Xian-Yong; Chinese Chemical Letters; (2020);,
Bromide – Wikipedia,
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Related Products of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1512-{4-[4-(2-methoxyphenyl)piperazin- I -yI]-1 H-pyrazolo[3,4-d]pyrimidin- I -yI}-N,Ndimethylaniline 80 mg (0.26 mmo[) 4-[4-(2-methoxypheny[)piperazin-1 -y[]-1 H-pyrazo[o[3,4-d]pyrimidine, 77.4 mg (0.39 mmo[) 2-bromo-N,N-dimethy[ani[ine, 14.7 mg (0.08mmo[) copper(I) iodide, 115 mg (0.54 mmo[) tripotassium phosphate and 22mg (0.16mmo[) trans-N,N?-dimethy[cyc[ohexane-1,2-diamine in 3 mL anhydrous NMP wereheated under microwave irradiation at 180CC for 8 h. The reaction mixture waspoured into water and extracted three times with ethy[ acetate. The combinedorganic phases were washed with 0.5 M aqueous EDTA so[ution and three times with water, dried over magnesium su[fate and concentrated. The residue was purified by HPLC affording 3 mg (3%) product.LC-MS (ana[ytica[ method 3): R = 1 .09 mm, MS (ESipos): mlz = 430 (M+H).1H-NMR (300MHz, CHLOROFORM-d): 6 [ppm]= 2.52 (5, 6H), 3.25 – 3.33 (m, 4H), 3.96 (5, 3H), 4.22 – 4.30 (m, 4H), 6.92 – 7.16 (m, 6H), 7.31 (d, 1H), 7.36 – 7.45 (m, 1H), 8.25 (5, 1H), 8.45 (5, 1H).

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, 2-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; GOLZ, Stefan; TELSER, Joachim; REHWINKEL, Hartmut; SIEBENEICHER, Holger; BUCHMANN, Bernd; ZORN, Ludwig; EIS, Knut; KOPPITZ, Marcus; LINDNER, Niels; HEROULT, Melanie; NEUHAUS, Roland; WO2013/182612; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 176317-02-5, The chemical industry reduces the impact on the environment during synthesis 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, I believe this compound will play a more active role in future production and life.

(1-1) Synthesis of 2,3,4-trifluoro-1-[1-hydroxy-4-(trans-4-propylcyclohexyl) cyclohexyl]benzene Into 7.6 g of magnesium and 20 mL of THF which were stirred while water-cooling in a nitrogen atmosphere, a THF solution (200 mL) containing 60 g of 2,3,4-trifluorobromobenzene was added dropwise for 2 hours, and stirred for 3 hours. Into this, a THF solution (200 mL) containing 70 g of 4-(trans-4-propylcyclohexyl)cyclohexanone was added dropwise for 2 hours, and stirred for 2 hours. After the reaction solution was poured into 10% hydrochloric acid and stirred for a while, an organic layer was separated, and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure to obtain 110 g of 2,3,4-trifluoro-1-[1-hydroxy-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene (unsatisfactorily dried). MS m/z: 354 (M+), 55 (100)

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-Bromo-2,3,4-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dainippon Ink and Chemicals, Incorporated; EP1640433; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 133739-70-5 as follows. COA of Formula: C6H2BrF3

A solution of butyllithium (0.10 mol) in hexane was dropped in a mixture of 2,3,5-trifluoro-1-bromobenzene (0.10 mol) and THF 100 ml with maintaining a temperature of -78 C. and the mixture formed was stirred for 30 minutes at the same temperature. To this solution was dropped a solution of 4-pentylcyclohexanone (0.11 mol) in THF (50 ml) with maintaining a temperature of -78 C., the mixture formed was warmed up gradually to room temperature with stirring and stirred for 2 hours at room temperature. The reaced product was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After the solvent was distilled off, toluene (100 ml) and p-toluenesulfonic acid (5 g) was added to the residue and then the mixture formed was heat-refluxed with dehydration of water formed. After cooling, the organic phase was washed enough with water and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, ethanol (80 ml) and Raney nickel (3 g) were added to the residue and the mixture was stirred for 12 hours under hydrogen atmosphere. After it was confirmed that absorption of hydrogen was stopped, the catalyst was removed from the reaction system by filtration. The solvent was distilled off to give 1,2,5-trifluoro-4-(4-pentylcyclohexyl)benzene (89 mmol) in the form of oil as residue. This product was a mixture of cis/trans, however it was used in the subsequent reaction without purification.

According to the analysis of related databases, 133739-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chisso Corp.; US6117361; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69321-60-4, name is 2,6-Dibromotoluene, 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 69321-60-4, Quality Control of 2,6-Dibromotoluene

Example 27 3-Bromo-2-methylbenzoic Acid To a solution of 1,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at -80 C. Then reaction mixture was stirred between -76~-78 C. for 2 h. Then the mixture was cooled to below -80 C. and dry ice was added after which the mixture was warmed to room temperature naturally. Solvent was removed, 5% NaOH solution (40 mL) added and the aqueous solution was washed with CH2Cl2 (10 mL*2). Then the aqueous layer was acidified with concentrated HCl to pH=1 and extracted with EtOAc (100 mL*2). The combined organic extracts were dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chomatography, (eluted with petrol. ether: EtOAc=8:1 to 1:1), to obtain 3.58 g of the product. Yield: 63.4%. 1H NMR (400 MHz, CDCl3) delta 2.73 (s, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1H).

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, 2,6-Dibromotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 117718-84-0, name is 6-Bromoimidazo[1,2-a]pyrazin-8-amine, A new synthetic method of this compound is introduced below., name: 6-Bromoimidazo[1,2-a]pyrazin-8-amine

Step 1 : Preparation of 6-bromo-8-[bis[(l,l -dimethylethoxy)carbonyl]amino]imidazo[l,2- a]pyrazine6-bromo-8-[bis[(l , 1 -dimethylethoxy)carbonyl] amino] imidazo[l ,2-a]pyrazine was prepared from 6-bromoimidazo[l ,2-a]pyrazin-8-amine according to reference procedure for similar compound (Lind, Kenneth E. etc. WO2008005457).

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; MERCK SHARP & DOHME CORP.; MENG, Zhaoyang; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; WO2013/16160; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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.

4-bromophenol (8.6 g, 49.9 mmol), 4-phenylbutyl bromide (11.2 g, 52.6 mmol) and potassium carbonate (13.7 g, (40 ml) was added under stirring with N, N-dimethylformamide (40 ml). The reaction was heated to reflux and refluxed at reflux conditions The reaction was carried out for 2 hours. The reaction solution was cooled to room temperature, water (160 ml) was added, and the mixture was extracted with ether (100 ml x 2) to combine the organic phases. The organic phase was washed successively with 0.5 M sodium hydroxide solution (110 ml) and water (110 ml), dried over anhydrous sodium sulfate and filtered to remove The filtrate was concentrated under reduced pressure and the concentrate was purified by silica gel chromatography to give 11.3 g of the title compound in 74.3% yield.

The synthetic route of 13633-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Haibu Pharmaceutical Technology Co., Ltd.; Di Wei; Sun Fengqing; (17 pag.)CN107253903; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2Br2F2

Synthesis of H2 (p-F2-bdp). H2(p-F2-bdp) was prepared via a Suzuki-Miyaura coupling as generally depicted in Scheme 3. Specifically, 1,4-dibromo-2,5-difluorobenzene (2.18 g, 8.0 mmol, 1.0 equiv), 1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester (5.56 g, 20.0 mmol, 2.5 equiv), and K3PO4 (8.48 g, 40 mmol, 5 equiv) were suspended in toluene (16 mL) in a 40-mL glass scintillation vial with a magnetic stir bar and sparged with Ar for 10 minutes. XPhos Pd G2 (1.26 g, 1.6 mmol, 0.2 equiv) was added quickly in air, and vial was briefly purged with Ar, sealed with a PTFE-lined cap, and heated to 110 C. while stirring for 2 days. Upon completion, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with 250 mL of diethyl ether. The ether layer was washed 5 times with 250 mL of saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure to yield a yellow oil, which was used in the subsequent reaction without additional purification. The crude ligand was dissolved in 60 mL of methanol in a 250-mL round-bottom flask with a magnetic stir bar, 12 mL of concentrated aqueous HCl was added, and the reaction mixture was stirred at 50 C. for 2 h, during which time a white precipitate formed. The reaction mixture was filtered, and the filtrate was suspended in water and neutralized with NaHCO3. The precipitate was again isolated by filtration, washed with water, and dried in vacuo to yield H2(p-F2-bdp) (0.86 g, 3.5 mmol, 44%) as a beige powder. 1H NMR (400 MHz, DMSO-d6): delta 8.11 (s, 4H), 7.68 (t, J=9.3 Hz, 2H) ppm; 13C NMR (101 MHz, DMSO-d6): delta 156.06, 153.68, 132.40, 119.33-119.81 (m), 118.58-118.14 (m), 114.60-113.78 (m) ppm; 19F NMR (400 MHz, DMSO-d6): delta -119.78 (t, J=9.3 Hz) ppm. Note that the 1H NMR signals from the hydrogen atoms bonded to the pyrazole nitrogen atoms are too broad to be visible. Anal. Calcd. for C12H8F2N4: C, 58.54, H, 3.27, N, 22.75; found: C, 57.72, H, 3.35, N, 21.82. IR: 3139 (m), 3076 (w), 2966 (m), 2938 (m), 2850 (m), 1589 (m), 1539 (w), 1490 (m), 1435 (w), 1374 (m), 1350 (w), 1273 (m), 1241 (w), 1155 (s), 1041 (m), 963 (s), 867 (s), 818 (m), 780 (s), 698 (m), 668 (w), 605 (s), 549 (w), 531 (w), 512 (w), 482 (w), 472 (w), 460 (m) cm-1.

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of California; Long, Jeffrey R.; Mason, Jarad A.; Taylor, Mercedes K.; Oktawiec, Julia; (70 pag.)US2018/297010; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary