Tag: M.W=100-200

Application of 10485-09-3, The chemical industry reduces the impact on the environment during synthesis 10485-09-3, name is 2-Bromoindene, I believe this compound will play a more active role in future production and life.

General procedure: Into a 25 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.035 g, 2.0 mol %), ethyl 5-bromothiophene-2-carboxylate (0.47 g, 2.0 mmol), and 5.0 mL of 5-bromo-2-thienylzinc bromide (B) (0.5 M in THF, 2.5 mmol) under an argon atmosphere at room temperature. The resulting mixture was stirred at room temperature for 2 h. Quenched with 3 M HCl solution, then extracted with ethyl ether (10 mL × 3). Washed with saturated NaHCO3, Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (2% ethyl acetate/98% heptane) afforded 0.39 g of ethyl 5?-bromo-2,2?-bithiophene-5-carboxylate (3d) in 62% isolated yield as a yellow 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, 2-Bromoindene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jung, Hye-Soo; Cho, Hyun-Hee; Kim, Seung-Hoi; Tetrahedron Letters; vol. 54; 8; (2013); p. 960 – 964;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1647-26-3, 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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00319] A reaction vial was charged with N-(quinolin-3-yl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine (15.00 mg, 0.05428 mmol), 2-bromo ethylcyclohexane (10.4 mg, 0.0000543 mol), NN- diisopropylethylamine (0.0189 mL, 0.000108 mol) and acetonitrile (1 mL, 0.02 mol) and the reaction heated in a microwave at 120 0C for 1 h. The reaction was then quenched with water and extracted with dichloromethane. The solvent was removed and the residue purified by prep HPLC to get the product as peach colored solid. MS (M+H)= 386.9;1H-NMR (DMSOd6I3): (400 MHz) 59.09 (d, J=2.12Hz, IH), 8.70 (d, J=I .87 Hz, IH), 8.26 (s, IH), 7.98 (d, J=5.34 Hz, IH), 7.90 (d, J=8.85 Hz, IH), 7.83 (d, J=7.58 Hz, IH), 7.56-7.48 (m, 2H), 6.64 (d, 7=5.38 Hz, IH), 3.49 (s, 2H), 2.74 (s, 4H), 1.80-0.85 (m, 15 H)

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-cyclohexylethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RENOVIS, INC.; WO2009/11904; (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. 6911-87-1, name is 4-Bromo-N-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

To a microwave reaction vessel were added 2-aminopyridine-5-boronic acid pinacol ester (220 mg, 1.0 mmol), 4-bromo-N-methylaniline (184 mg, 1.0 mmol), 1,4-dioxane (4 mL) and 20% aq sodium carbonate (3 mL). Argon gas was bubbled through the solution for 5 min, then tetrakis(triphenylphosphine) palladium(O) (57 mg, 0.05 mmol) was added. The vial was sealed and heated in a microwave reactor for 30 min at 150 C. After cooling to rt, silica gel was added and the mixture was concentrated under reduced pressure. Purification by silica gel flash chromatography eluting with 1 :20 MeOH/ EtOAc gave 5-(4- (methylamino)phenyl)pyridin-2-amine (79 mg, 39%) as an off white solid. LC-MS (ESI) m/z 200 (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; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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 3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one (400 mg, 1.82 mmol) in anhydrous DMF (5 mL) was added K2CO3 (503 mg, 3.64 mmol) and (bromomethyl)cyclopentane (445 mg, 2.73 mmol). The reaction mixture was stirred at 60C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC-MS to afford 7-(cyclopentylmethyl)-3-(tetrahydro-2/-/-pyran-4-yl)imidazo[1 ,5- a]pyrazin-8(7H)-one 290 mg (53%). NMR (DMSO-de, 400 Mhz): delta 7.62 (s, 1 H), 7.49 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.91 -3.88 (m, 2H), 3.69 (d, J = 7.6Hz, 2H), 3.48-3.43 (m, 2H), 3.42-3.31 (m, 1 H), 2.27- 2.24 (m, 1 H), 1.78-1.73 (m, 4H), 1.58-1.44 (m, 6H) , 1.21 -1.20 (m, 2H). LC-MS: (m/z) 302.2 (MH+) tR (minutes, method 3) = 2.29 minutes .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopentane, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51437-00-4, 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 51437-00-4 as follows.

To a solution of diisopropylamine (1.77g, 17.5 mmol, 1.1 eq) in THF (20 mL) was added n-BuLi (7.3 mL, 2.4 M in THF, 17.5 mmol, 1.1 eq) at -78C under N2. The mixture was stirred at -78C for lh, then a solution of 4-bromo-l-fluoro-2 -methyl-benzene (3 g, 15.8 mmol, 1.0 eq ) in THF (20 mL) was added dropwise. The reaction was stirred a further 2h at -78C then C02 gas was bubbled into the mixture for 30 min. The reaction was quenched by addition of water and acidified to pH 3 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue obtained was purified by chromatography to give the title compound as a white solid (697 mg, 21 %).LC-MS : m/z 230.9, 232.9 [M-H]” HNMR (400 MHz, DMSO-d6) ? 7.94 – 7.59 (m, 2H), 2.26 (s, 3H)

According to the analysis of related databases, 51437-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10269-01-9, The chemical industry reduces the impact on the environment during synthesis 10269-01-9, name is (3-Bromophenyl)methanamine, I believe this compound will play a more active role in future production and life.

(4?-(Trifluoromethyl)biphenyl-3-yl)methanamine. A 1 00-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with (3- bromophenyl)methanamine (570 mg, 3.0 mmol), 4-(trifluoromethyl)phenylboronic acid (558 mg, 3.0 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol), K3P04 (1.91 g, 9.0 mmol), DME (30 mL) and H20 (6 mL). The system was subject to 3 cycles of vacuum/argon flush and heated at reflux for overnight. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:20 MeOH/CH2C12 to afford the title compound (640 mg, 85%) as brown solid. MS-ESI: [M+H] 252.1.

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, (3-Bromophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-46-1, 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. 766-46-1, name is 2′-Bromophenylacetylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

under high purity nitrogen atmosphere, into 10ml of Schlek reaction tube was 0.02mmol benzoquinolin triphenylphosphine ring iridium hydrogen adduct material (4), 1mmol2- bromophenyl acetylene, 2mmol benzyl alcohol, and 1.0 mmol of potassium carbonate in 3ml of toluene, the reaction tube was replaced with nitrogen 3 times, then in an oil bath with magnetic stirring and heated to 110 deg.] C, the reaction was refluxed for 20 hours. Oil bath was removed, the water bath to room temperature; 3ml adding water to the reaction liquid, extracted three times with 5ml of dichloromethane, and the combined organic phases were dried over anhydrous MgSO4 for 30 minutes and filtered; the filtrate was concentrated on a rotary evaporator, the remaining oil residue ether as eluent, separated by thin layer chromatography on silica gel to give the pure product 1-phenyl-3 (2-bromophenyl) -1-propanone, yield 88%.

The synthetic route of 2′-Bromophenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luoyang Normal University; Li, Xiao Dong; Li, gongmei; Xu, Chen; Hao, Xin Qi; Xiao, Zhi Qiang; (10 pag.)CN103242372; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4, Quality Control of 4-Bromo-1-fluoro-2-methylbenzene

Step 1. 5-Bromo-2-fluoro-3-methylbenzaldehyde: To a stirred solution of di- isopropyl amine (4.01 g, 39.88 mmol) in THF (20 mL) was added n-butyl lithium (1.6 M in hexane) (19.9 mL, 31.91 mmol) at -78 C slowly dropwise over the period of 10 min, the reaction mixture was stirred at -78C for 30 min. A solution of 4-bromo-l-fluoro-2- methylbenzene (5.0 g, 26.6 mmol) in THF (30.0 mL) was added at -78C, and the reaction mixture was stirred for lh at the same temperature. DMF (5.0 mL) was added and stirred at – 78C for another 30 min. The reaction was monitored by TLC; then the reaction mixture was quenched with IN HC1 solution (aq) at 0C. The aqueous layer was extracted with diethyl ether, washed with water and saturated brine solution. The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude compound purified by flash column chromatography (Si02, 100-200 mesh; eluting with 5% ethyl acetate/ pet ether) to afford the title compound as a white solid (3.6 g, 64 ); mp 48- 50C: ]H NMR (400 MHz, CDC13) delta 8.33 (s, 1H), 8.22 (s, 1H), 7.67 (s, 1H), 7.60 (s, 1H), 6.75 (dd, J = 17.6, 10.8 Hz, 1H), 5.92 (dd, J = 17.6, 10.8 Hz, 1H), 5.52 (d, J = 17.6 Hz, 1H), 2.21 (s, 3H); ESIMS m/z 211.35 ([M-H]”).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-fluoro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, category: bromides-buliding-blocks

4-Chlorophenylboronic acid (20.2 g, 0.13mol) and tetrakis(triphenylphosphine)palladium (0) (3.7g, 0.003 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2- dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 200C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 5-(4- chlorophenyl)-2-methylaniline (21.0 g).

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; SYNGENTA PARTICIPATIONS AG; WO2008/110307; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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. name: 1-Bromo-2,3-difluorobenzene

General procedure: In a 15 mL sealed tube equipped with a magnetic stirring bar were added 1 (1 mmol),2 (0.8 mmol), tert-butyl isocyanide (1.2 mmol, 136 muL), Pd(OAc)2 (0.03 mmol, 7 mg),DPEPhos (0.06 mmol, 32 mg), Cs2CO3 (0.8 mmol, 261 mg), and anhydrous DMF (2.0mL). The tube was purged with argon, and the contents were stirred at 100 °C for 2 h.Then Na2S*9H2O (1.2 mmol, 240 mg) was added for 2 h. After reaction completion,the mixture was filtered through a pad of Celite, and DMF was removed by a vacuum.The combined filtrates were refluxed in THF (15 mL) and oxalic acid (1 M, 3 mL) for 8h. The solvents were removed under reduced pressure, then poured into brine (20mL) and extracted by ethyl acetate (3 × 30 mL). The combined organic layers weredried (Na2SO4) and evaporated. The residue was purified on a silica gel column usingpetroleum ether/ethyl acetate as the eluent to give the pure target product.

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Fang-Ling; Chen, Zhen-Bang; Liu, Kui; Yuan, Qing; Jiang, Qing; Zhu, Yong-Ming; Synlett; vol. 29; 5; (2018); p. 621 – 626;,
Bromide – Wikipedia,
bromide – Wiktionary