Category: 69321-60-4

Application of 69321-60-4, 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 69321-60-4 as follows.

A 100-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 102b (1.00 g, 5.37 mmol), (2.69 g, 10.7 mmol), cesium carbonate (3.49 g, 10.7 mmol), N,N’-dimethylethylenediamine (473 mg, 5.37 mmol) and 1 ,4-dioxane (45 mL). After bubbling nitrogen through the resulting suspension for 30 min, copper iodide (510 mg, 2.69 mmol) was added, and the reaction mixture was heated at 105 C (oil bath temperature) for 14 h. After this time, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (200 mL) and water (40 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 62% yield (1.18 g) of 102c as an off-white solid: mp 178-180 C; ]H NMR (300 MHz, CDC13) delta 7.74 (dt, 1H, / = 8.2, 1.0 Hz), 7.58 (dd, 1H, / = 7.8, 1.2 Hz), 7.37 (m, 3H), 7.19 (m, 3H), 4.45 (m, 2H), 4.21 (m, 1H), 3.95 (m, 1H), 2.38 (s, 3H); MS (ESI+) m/z 355.0 (M+H).

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.362 g 2,6-dibromo-toluene (9.45 mmol) was dissolved in 10 mL dry THF under N2 atmosphere and the mixture was cooled to -78 C. Then 5.2 mL nBuLi (2.OM in pentane,10.4 mmol) was added dropwise and the mixture was stirred for 15 minutes. Then 2.31 mL2-isopropoxy-4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane (11.3 mmo 1) was added dropwise and the mixture was allowed to warm up to r.t.. It was stirred until no further conversion was observed. Then the mixture was quenched with aqueous NH4C1 solution, then extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and thefiltrate was concentrated under reduced pressure. The crude product was purified via flash chromatography using heptane and EtOAc as eluents to obtain Preparation B7. 1H NMR(400 MHz, CDC13) oe: 7.67 (d, 1H), 7.62 (d, 1H), 7.10 (t, 1H), 2.53 (s, 3H), 1.29 (s, 12H)

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; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; SZLAVIK, Zoltan; SZABO, Zoltan; CSEKEI, Marton; PACZAL, Attila; KOTSCHY, Andras; BRUNO, Alain; GENESTE, Olivier; CHEN, I-Jen; DAVIDSON, James Edward Paul; MURRAY, James Brooke; ONDI, Levente; RADICS, Gabor; SIPOS, Szabolcs; PROSZENYAK, Agnes; PERRON-SIERRA, Francoise; BALINT, Balazs; (188 pag.)WO2016/207226; (2016); A1;,
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

Synthetic Route of 69321-60-4, 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 69321-60-4 as follows.

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was purged with nitrogen and charged with 2,6-dibromotoluene (2.50 g, 10.0 mmol), N-bromosuccinimide (1.78 g, 10.0 mmol) and carbon tetrachloride (40 mL). The solution was heated to 80 C (oil bath temperature), and 2,2′-azobisisobutyronitrile (164 mg, 1.00 mmol) was added. The resulting mixture was refluxed for 14 h. After that time, the mixture was cooled to room temperature and filtered. The filter cake was washed with carbon tetrachloride (2 x 20 mL). The filtrate was diluted with ethyl acetate (200 mL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford a quantative yield (3.28 g) of l,3-dibromo-2-(bromomethyl)benzene as a yellow solid: mp 77-78 C; ]H NMR (300 MHz, CDC13) delta 7.55 (d, 2H, / = 8.1 Hz), 7.07 (t, 1H, J = 8.1 Hz), 4.83 (s, 2H).

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy, B.; WO2012/30990; (2012); A1;,
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, SDS of cas: 69321-60-4

A mixture of 1,3-dibromo-2-methylbenzene (Combi-Blocks catOT-1437: 143 mg, 0.573 mmol), tert-butyl 4-ethynylpiperidine-1-carboxylate (ArkPharm catalog AK-34528: 60 mg, 0.287 mmol), copper(I) iodide (4.37 mg, 0.023 mmol), dichlorobis(triphenylphosphine)-palladium( II) (26.8 mg, 0.038 mmol), and triethylamine (0.080 ml, 0.573 mmol) in 1,4-Dioxane (3.0 ml) was flushed with N2. The resulting slurry was stirred at 90 C. for 3 h. The reaction was then quenched with water, extracted with EtOAc (3¡Á15 mL). The organic layers were combined, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel, eluting with 0-35% ethyl acetate/hexanes, to give the desired product. LC-MS calculated for C15H17BrNO2 (M+H-tBu)+: m/z=322.0; found 322.0.

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; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); 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. 69321-60-4, name is 2,6-Dibromotoluene, A new synthetic method of this compound is introduced below., Recommanded Product: 69321-60-4

A mixture of 1,3-dibromo-2-methylbenzene (6.0 g, 24 mmol), phenylboronic acid(2.9 g, 24 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexedwith dichloromethane (1: 1) (817 mg, 1. 0 mmol) and potassium carbonate (1 0 g, 725 mmol) in 1,4-dioxane (100 mL) and water (70 mL) was stirred at room temperatureovernight. The reaction was quenched with water, and extracted with ethyl acetate (3x 150mL). The combined organic layers were washed with brine, dried over Na2S04, filtered andconcentrated under reduced pressure. The residue was purified by chromatography on silicagel, eluting with 0-5% EtOAc/hexanes, to give the desired product (4.7 g).

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; INCYTE CORPORATION; LU, Liang; QIAN, Ding-Quan; WU, Liangxing; YAO, Wenqing; (103 pag.)WO2017/205464; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

69321-60-4, name is 2,6-Dibromotoluene, 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. 69321-60-4

A 50-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with ethyl l-(2-aminoethyl)-4, 5,6,7- tetrahydro-lH-indole-2-carboxylate 101k (560 m g, 2.95 mmol), 2,6-dibromotoluene (1.47 g, cesium carbonate (1.92 g, 5.90 mmol), N,N’-dimethylethylenediamine (260 mg, 2.95 mmol) and 1,4-dioxane (25 mL). After bubbling nitrogen through the resulting suspension for 30 min, copper N,N’-dimethylethylenediamine (260 mg, 2.95 mmol) was added, and the reaction mixture was heated at 105 C (oil bath temperature) for 14 h. After this time, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (100 mL) and water (20 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by columnchromatography to afford a 57% yield (600 mg) of 2-(3-bromo-2-methylphenyl)-3,4,6,7,8,9- hexahydropyrazino[l,2-fl]indol-l(2H)-one 1011 as a white solid: mp 163-165 C; ‘H NMR (500 MHz, DMSO-i? delta 7.57 (dd, 1H, J = 8.0, 0.5 Hz), 7.32 (d, 1H, J = 7.5 Hz), 7.21 (t, 1H, J = 8.0 Hz), 6.50 (s, 1H), 4.11 (m, 3H), 3.75 (m, 1H), 2.59 (m, 2H), 2.45 (m, 2H), 2.21 (s, 3H), 1.78 (m, 2H), 1.68 (m, 2H); (APCI+) m/z 358.6 (M+H)

Statistics shows that 69321-60-4 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromotoluene.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 69321-60-4, name is 2,6-Dibromotoluene, 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. 69321-60-4

6-Dimethylamino-3,4-dihydro-2H-isoquinolin-l-one (150mg, 0.789mmol), cuprous iodide (30mg, O.lbetammol) and potassium carbonate (109mg, 0.789mmol) were deposited in a sealed vessel. 3 mL DMSO and 2,6-dibromotoluene (395mg, 1.58mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 1500C for 24 hours. Cuprous iodide (30mg, O.lbetammol) was added and the mixture was heated at 1500C for an additional 24 hours. This was diluted with dichoromethane and filtered through a pad of celite. The filtrate was partitioned between DCM and 5% aq. ammonium hydroxide. The DCM layer was washed with brine. The combined aqueous layers were washed with DCM. The combined DCM layers were dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 25 to 50% ethyl acetate/hexanes) to yield 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-l-one (181mg, 0.504mmol). MS (ESI) 361.1 (M+H)+.

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 2,6-Dibromotoluene.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/98144; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary