Category: 1996-30-1

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3BrClF

To a mixture of 2-bromo-4-chloro-l-fluorobenzene (2 g, 9.55 mmol) and liT-pyrazole (0.618 g, 9.07 mmol) in DMF (20 mL) was added Cs2C03(6.22 g, 19.10 mmol). The reaction mixture was stirred at 90C for 1 hour. LCMS showed the reaction was completed. The reaction was cooled to 25C, diluted with EtOAc (30 mL) and water (30 mL). The aqueoUs layer was extracted with EtOAc (2 x 30 mL). The combined organic phase was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica (0-10% EtOAc/petroleum ether) to give the title compound.

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; DEBENHAM, John, S.; ZHU, Cheng; (64 pag.)WO2020/86416; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

890 p1 (7.0 mmol) of 2-bromo-4-chloro-1-fluorobenzene, 720 mg (7.02 mmol) of 4-chloro-1H- imidazole, 2.91 g (21.1 mmol) of potassium carbonate and 30 ml DMF were divided into twomicrowave vessels and stirred in the microwave at 130C for 3 hours. After cooling, the two reaction mixtures were combined and 150 ml of cold water were added with stirring. This mixture was stirred for 5 mm. The suspension was then filtered and the solid was washed with ice-water and pentane and dried under high vacuum. Yield: 1.33 g (64% of theory)LC/MS [Method 1]: R = 0.97 mm; MS (ESIpos): m/z = 293 (M+H),?H-NMR (400 MHz, DMSO-d6): oe [ppm] = 8.05 (d, 1H), 7.89 (d, 1H), 7.68-7.59 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ NUNEZ, Eloisa; ACKERSTAFF, Jens; ROeHRIG, Susanne; HILLISCH, Alexander; MEIER, Katharina; HEITMEIER, Stefan; TERSTEEGEN, Adrian; STAMPFUSS, Jan; ELLERBROCK, Pascal; MEIBOM, Daniel; LANG, Dieter; (399 pag.)WO2017/5725; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1996-30-1, 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00227] Step 12. 3-Bromo-5-chloro-2-fluorobenzaldehyde. A solution of 2,2,6,6- tetramethylpiperidine (327 g, 98%, 2.274 mol) and THF (1.9 L, HPLC grade) was cooled to -75 0C (dry ice-methanol bath) under an argon atmosphere. 1.6 M n-BuLi/hexane solution (1.47 L, 2.35 mol) was added slowly into the mixture at -72 to -67 0C over 1 h. The mixture was stirred at -72 to -67 0C for 30 min to give a pale yellow suspension. 2-Bromo-4-chloro-l-fluorobenzene (435 g, 97%, 2.02 mol) was added slowly into the mixture at -72 to -67 0C over 30 min, and then the mixture was stirred at -72 to -67 0C for an additional 30 min. Dimethylformamide (230 g, 99.5%, 3.14 mol) was added slowly into the mixture at -70 to -65 0C over 30 min and then the mixture was stirred at -70 to -65 0C for 30 min to afford a light brown solution. The cooling bath was removed and then saturated ammonium chloride solution (720 mL) was added into the batch at -60 to -30 0C over 15 min to obtain a hazy mixture. 6 N hydrochloric acid was quickly added into the mixture at -30 to 10 0C over 15 min to pH 1 and then ethyl acetate (2.0 L) was added at 10 to 20 0C. The layers were separated and the aqueous layer was extracted with ethyl acetate (1 x 300 mL). The combined organic extracts were washed with water (I x 800 mL) and brine (I x 500 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated under vacuum (60-65 0C) to give the title compound as a tan viscous oil, which solidified upon standing after several hours. 1H NMR (CDCl3): delta 7.76-8.30 (m, 2H), 10.0-10.8 (br s, IH); MS m/z 238.0 (M+l).

The synthetic route of 3-Bromo-4-fluorochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG; HUANG, Shenlin; JIN, Xianming; LIU, Zuosheng; POON, Daniel; TELLEW, John; WAN, Yongqin; WANG, Xing; XIE, Yongping; WO2011/25927; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., 1996-30-1

A mixture of 2-30 (1.04 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified by column chromatography on silica gel eluting with PE/ethyl acetate from 20/1 to 10/1 to provide intermediate 2-31 (806 mg, 63% yield) as a yellow solid. LCMS (m/z): 173 [M-H-82j -.

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; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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. 1996-30-1.

[0136] A solution of 2-bromo-4-chloro-1-fluorobenzene (175 muL, 1.377 mmol) in THF (4.59 mL) at 78 C. was treated with n-BuLi (2.6 M, 741 muL, 1.928 mmol) and the reaction mixture was stirred for 30 min. To this was added tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (250 mg, 0.918 mmol) in one portion. The cooling bath was removed and the resulting reaction mixture was allowed to warm to rt and stirred for 1.5 h. Purification by automated flash silica gel chromatography using 10% EtOAc in hexanes afforded tert-butyl 4-(5-chloro-2-fluorobenzoyl)piperidine-1-carboxylate (287.9 mg, 92%) as a yellow oil. ESI-MS m/z [M+Na]+ 364.20

The synthetic route of 3-Bromo-4-fluorochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Brown, Jason; Hitchcock, Steve; Hopkins, Maria; Kikuchi, Shota; Monenschein, Holger; Reichard, Holly; Schleicher, Kristin; Sun, Huikai; Macklin, Todd; US2015/175602; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-30-1, Name is 3-Bromo-4-fluorochlorobenzene, 1996-30-1, belongs to chlorides-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.

To a solution of 2-bromo-4-chloro-1 -fluorobenzene (1 .03 g, 4.94 mmol) in tetrahydrofuran (20 ml_) at -78 C was added n-butyllithium (4.0 ml_, 9.88 mmol) under nitrogen. The reaction mixture was stirred at -78 C for 2 h before a solution of 6-(4-methoxybenzylamino)pyridazine-3-carbaldehyde (0.800 g, 3.29 mmol) in tetrahydrofuran (3 ml_) was added dropwise. The reaction mixture was stirred for another 2 h and was warmed to 20 C. Aqueous ammonium chloride was added to quench the reaction and the volatiles were removed under reduced pressure. The aqueous layer was extracted with dichloromethane (50 ml_ x 2). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude sample was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4/1 to 1 /1 ) to give (5-chloro-2-fluorophenyl)(6-(4-methoxybenzylamino)pyridazin-3-yl)methanol (0.330 g, 0.888 mmol, 27%) as a yellow solid. LCMS (ESI) m/z: 374.0 [M+H]+.

Statistics shows that 3-Bromo-4-fluorochlorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-30-1.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1996-30-1

Step 1. l-(2-Bromo-4-chlorophenyl)-lH-l,2,3-triazole. To a solution of 2-bromo-4-chloro-l- fluorobenzene (5 g, 24 mmol) and 2H-l,2,3-triazole (6.60 g, 95 mmol) in DMF (2 mL) was added K2CO3 (16.50 g, 119 mmol). The mixture was stirred at 100C for 13 h under N2 atmosphere. The mixture was diluted with water (10 mL) and extracted with EtOAc (10 mL x 2). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (Si02, PE: EtOAc = 100: 1 to 3: 1) to give the title compound. MS (ESI) m/z 260.0 (M+H).

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Weiguo; EDMONDSON, Scott, D.; GUO, Zhuyan; MERTZ, Eric; OGAWA, Anthony, K.; SO, Sung-Sau; SUN, Wanying; BROCKUNIER, Linda, L.; ALI, Amjad; KUANG, Rongze; WU, Heping; WO2015/183709; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 1996-30-1

2-fluoro-5-chlorobromobenzene 18a (11.0g, 52.8mmol), ethynyltrimethyl Silane (7.7 g, 79 mmol) and triethylamine (60 mL) were mixed, and then cuprous iodide (100 mg, 0.53 mmol) and ditriphenylphosphine palladium chloride (1.86 g, 2.65 mmol) were added.The reaction mixture was heated to 80 C under a nitrogen atmosphere and stirring was continued for 4 hours.After the reaction was completed, the solution was desolvated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 100/1) to obtain the target product ((2-fluoro-5-chlorophenyl) ethynyl) trimethyl. Silane 18b (11.0 g, yellow oil), yield: 90%.

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; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., 1996-30-1

Carbazole (800 mmol, 133.8 g), 2-bromo-4-chloro-1-fluorobenzene (840 mmol 175.9 g), and dimethylformamide (160 ml) were added to a three-necked flask, and the flask was flushed with nitrogen. Sodium hydride (62% paraffin dispersion) (800 mmol, 31.0 g) was added thereto stepwise five or more times, while observing the amount of hydrogen gas generated, and the reaction mixture was slowly heated while observing the amount of hydrogen gas generated. The reaction mixture was then heated under stirring at a temperature of 150 C. for 20 hours. The reaction mixture was cooled to room temperature, diluted with toluene (1 L), and quenched with a small amount of water in a nitrogen atmosphere. The reaction mixture was filtered by using celite and washed three times with water by using a separatory funnel. The reaction mixture was dried by using anhydrous magnesium sulfate, filtered through a silica gel pad, and then, concentrated. The resultant obtained therefrom was recrystallized in a mixed solvent of ethanol_methanol=1:1 to obtain Intermediate 1-3. The amount of Intermediate 1-3 obtained was 156.1 g and the yield of Intermediate 1-3 was 55%.

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; Samsung Electronics Co., Ltd.; INAYAMA, Satoshi; IRISA, Shiro; KORAI, Keisuke; SAKURAI, Rie; ITO, Mitsunori; NUMATA, Masaki; (265 pag.)US2019/214570; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1. 1996-30-1

Intermediate 7A. 3-Chloro-l-(5-chloro-2-fluorophenyl)propan-l-one: In a flame-dried 3 -neck flask, 2-bromo-4-chloro-l-fluorobenzene (2.0 g, 9.55 mmol) was dissolved in THF (anhydrous) (28.9 mL) under argon. Isopropylmagnesium chloride (2 M in THF) (5.01 mL, 10.03 mmol) was added, and the reaction was stirred at rt. To this solution was added zinc chloride (0.5 M in THF) (20.44 mL, 10.22 mmol) and the mixture was stirred at ambient temperature for 40 min. To the reaction was then added Pd(PPh3)4 (0.276 g, 0.239 mmol), and the mixture was cooled to 0 C. A solution of 3- chloropropanoyl chloride (0.981 mL, 10.22 mmol) in THF (2.89 mL) was added, and the reaction was stirred for 2 h at 0 C. The reaction mixture was then quenched with 3 N HCl, diluted with water, and extracted with Et20 (3x). The combined organics were dried (MgS04), filtered and evaporated to yield a grainy yellow liquid, which was purified using silica gel chromatography to obtain a colorless oil, 3-chloro-l-(5-chloro-2- fluorophenyl)propan-l-one (0.405 g, 19%). MS (ESI) m/z: 221.0 (M+H)+. 1H NMR (400 MHz, CDC13) delta 7.88 (dd, J = 6.3, 2.8 Hz, 1H), 7.51 (ddd, J = 8.8, 4.3, 2.8 Hz, 1H), 7.13 (dd, J = 10.2, 8.7 Hz, 1H), 3.94 – 3.88 (m, 2H), 3.46 (td, J = 6.6, 3.2 Hz, 2H) ppm.

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 3-Bromo-4-fluorochlorobenzene.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAM, Patrick Y.S.; CLARK, Charles G.; CORTE, James R.; EWING, William R.; GILLIGAN, Paul J.; JEON, Yoon; YANG, Wu; SMITH, Leon, M., II.; WANG, Yufeng; WO2013/22814; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics