Category: 36282-26-5

Electric Literature of 36282-26-5, A common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at -78 C was added EtMgBr (18.3 mL,55 mmol) drop wise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et20 (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HC1 solution, and washed with EtOAc. The aqueous layer was adjusted to pH~10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3 x). The combined organic layers were dried over anhy.Na2S04, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 36282-26-5, 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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Pyrrole intermediates 3a-j, or 7a-p or 7s (0.7 mmol) and 2-bromo-4-fluorobenzonitrile (0.7 mmol) were dissolved in 0.5 mL of dry dimethyl formamide (DMF) in a round bottom flask. Sodium hydride (60% dispersion in oil) (0.7 mmol) was then added into the stirring reaction mixture under argon. After 4 h 10 mL of water was added to the reaction mixture and extracted using ethyl acetate (2 x 15 mL). The organic layers was washed with brine and dried over sodium sulfate followed by concentration. column chromatography (SiO2) was performed utilizing 20% ethyl acetate in hexanes to obtain products as amorphous solids

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-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, belongs to nitriles-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 36282-26-5, name: 2-Bromo-4-fluorobenzonitrile

5,4′-Difluoro-biphenyI-2-carbonitrie (CAB06058)A mixture of 2-bromo-4-fiuorobenzinitrile (5.0 g, 25.0 mmol), 4-fiuorophenylboronic acid (3.85 g,27.5 mmol), dimethoxyethane (30 rtiL) and 2M Na2CO3 (40 mL) was heated to reflux before Pd2(dba)3 (0.10 g) was added and heating was continued for 5 hours. After cooling to room temperature CHCl3 (50 mL) was added to and the mixture was filtered (celite). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography [SiO2, CHCl3] followed by recrystallisation from CHCl3/n-hexane to afford CAB06Theta58 (4.03 g, 71%) as colorless needles. Mp. 111-113 C; 1H NMR (400 MHz, CDCl3) delta 7,12-7.23 (m, 4H)3 7.50-7.56 (m, 2H), 7,76 (dd, J = 8.6, 5.4 Hz, IH); LRMS (ES+): m/z 416.0 (100%, [M+H]+); HRMS (ES+) calcd for Ci3H8F2N [M+H]+: 216,0619, found 216.0613; Anal, Calcd for Cj3H7F2N: C, 72.56; H3 3.28; N, 6.51. Found C, 72.4; H, 3.28; N3 6.55.

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; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrFN

4-Fluoro-2-(2-oxooxazolidin-3-yl)bejizonitrile. A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 0C for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes-.ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.73 (IH, dd, J = 5.8, 8.6 Hz), 7.43 (IH, dd, J = 2.5, 9.6 Hz), 7.11 (IH, ddd, J = 2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J = 7.1 Hz), 4.29 (2H, t, J = 7.1 HJz); LCMS f ESI, M+H*) m/z 207.

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.

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 36282-26-5 as follows. Computed Properties of C7H3BrFN

2-(Benzofuran~2-yl)~4-fluorobenzonitriIe (AUPOl 158-1)A mixture of 2-bromo-4-fluorobenzonitrile (5,15 g, 25.65 mmol), benzofuran-2- ylboronic acid (5.0 g, 30,8 mmol), 1 ,2-dimethoxyethane (25 mL) and 2M Na2CO3 (40 niL) was heated to reflux before Pd2(dba)3 (100 mg) was added and heating was continued for 5 h. After cooling to r.t, EtOAc (20 mL) was added to dissolve the product. The mixture was filtered through celite, the organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure, The residue was dissolved in minimum amount of CHCl3 and passed through Silica. Solvent was evaporated and the residue was first purified by crystallisation from a mixture CHCI3/PE (98/2). The filtrate was purified by Combiflash chromatography (40 g column, 13 g Silica, gradient of eluent from PE to PE/EtOac 9/1) to give the title compound as light yellow solid purified by rinsing with PE to give at the end a white solid (5.15 g), This solid had to be purified an ultimate time by drying under vacuum at 80 0C for O/N. Finally, pure expected compound was obtained as a off-white solid in 59% yield (3.6 g); mp 123-124 0C; 1H NMR (270 MHz, CDCl3) .57.13 (IH, td, J = 2.5 and 7.3 Hz, ArH), 730 (IH, X, J = 1.1 Hz5 ArH), 7,40 (IH, X, J = 1.1 Hz, ArH), 7.56 (IH5 d, J = 7.7 Hz, ArH), 7,69 (IH, d, J = 7.7 Hz, ArH), 7.76-7.86 (3H, m, ArH); Anal. Calcd. for Ci5H8FNO: C 75,94, H 3.40, N 5.90. Found: C 75,70, H 3.37, N 5.97 %.

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Synthetic Route of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Pyrrole (2, 6, 6-trimethyltetrahydroindol-4-one) (1.5 g, 8.5 mmol) and 2-bromo-4-fluorobenzonitrile (1.69 g, 8.5 mmol) were dissolved in anhydrous DMF (50 mL) . To this NaH (95%, 408 mg, 17.0 mmol) was added and stirred at 50 0C for 1 h. The reaction mixture was cooled to RT and H2O was added. Product crashed out of solution and was filtered and dried under vacuo (2.4 g, 79%). (100% clean by LCMS, product M+H = 357).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Method 10B: the bromophenol was prepared using the appropriate fluorobromobenzene with methanesulfonylethanol.Under inert atmosphere, to a solution of the fluorinated derivative in dimethylformamide was added methylsulfonylethanol (1.5eq). The mixture was stirred at 0 C. before adding sodium hydride (5eq). The reaction mixture was stirred at room temperature, then acidified with 1M hydrochloric acid solution to pH 2, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 10.4. 2-bromo-4-hydroxybenzonitrile Prepared following the method previously described (Method 10B) using 2-bromo-4-fluorobenzonitrile. The product was chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 90/10 to 80/20). The product was obtained as a white solid. Yield: 95% Rf (petroleum ether/ethyl acetate 70/30): 0.25 NMR 1H (CDCl3): 5.95 (s, 1H); 6.87 (dd, 1H, J=8.5 Hz, J=2.4 Hz); 7.17 (d, 1H, J=2.4 Hz); 7.54 (d, 1H, J=8.5 Hz).

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; GENFIT; US2010/4159; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2 dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 C. for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) ? ppm: 7.73 (1H, dd, J=5.8, 8.6 Hz), 7.43 (1H, dd, J=2.5, 9.6 Hz), 7.11 (1H, ddd, J=2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J=7.1 Hz), 4.29 (2H, t, J=7.1 HJz); LCMS (+ESI, M+H+) m/z 207.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, belongs to nitriles-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 36282-26-5, COA of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol) in anhydrous THF (20 mL) is added PrMgCl 2.0M in THF (15.0 mL, 30.0 mmol) at -30C. The solution is stirred at -30 C for 3 hours and DMF (5.80 mL, 75.0 mmol) is added. The reaction mixture is allowed to warm to room temperature and is stirred for 1 hour. The solution is cooled to -10C, 2M hydrochloric acid (37 mL) is added and the solution is stirred for 20 minutes. The solution is concentrated in vacuo to -1/3 original volume and extracted into EtOAc (3x). The combined organics are then dried (Na2S04), filtered and concentrated to afford 4-fluoro-2-formyl benzonitrile (3.9 g, 71%).

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-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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. name: 2-Bromo-4-fluorobenzonitrile

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) in ether (100 mL) was added MeMgBr (25 mL, 75 mmol) at room temperature. The solution was stirred at room temperature for 0.5 hour before Ti(Oi-Pr)4 (41 mL, 25 mmol) was added and the resulting mixture was heated to reflux for 6 hours. Aqueous NaOH (10%, 200 mL) solution was then slowly added to the reaction mixture at 0 C and the reaction mixture was stirred at room temperature for additional 30 minutes. After dilution with aq. Na2C03 (5%, 400 mL) solution, it was extracted with t-BuOMe (100 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue obtained was diluted with aq. HC1 solution (5%) and the aqueous layer was washed with t-BuOMe (50 mL x 2) and basified with 20% aq. NaOH to pH~ 10. The resulting aqueous layer was further extracted with t-BuOMe (100 mL x 3). The combined organic layers were then dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography to give the title product (3.0 g, yield 51.7%) as yellowish oil. MS: 231.7 (M+H+, IBr)

The synthetic route of 2-Bromo-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts