Category: 138642-47-4

Electric Literature of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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 138642-47-4, Computed Properties of C8H6BrNO

B. Synthesis of 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of 2-bromo-5-methoxybenzonitrile (82.6 g, 0.39 mol, 1 equiv), bis(pinacolato)diboron (109.1 g, 0.43 mol, 1.1 equiv) and potassium acetate (115.3 g, 1.17 mol, 3 equiv) in a mixture of 1,4-dioxane (400 mL) and DMSO (40 mL) was sparged with nitrogen for 1 hour. Pd(dppf)Cl2 (7.13 g, 5 mol %) was added and reaction mixture was gently heated at 60 C. for 2 hours then refluxed for 16 hours. The mixture was filtered through celite and the solids isolated from the filtrates were washed with isopropanol and heptanes to give the desired product as an off-white solid (57.41 g, 57% yield). Additional product (?10 g) was isolated from the filtrates.

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-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; BROOKS, Jason; SZIGETHY, Geza; MORELLO, Glenn; DENG, Jun; DJUROVICH, Peter I.; CHEN, Hsiao-Fan; (206 pag.)US2016/72082; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 138642-47-4, 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. 138642-47-4 name is 2-Bromo-5-methoxybenzonitrile, 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: To a mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 138642-47-4 as follows. HPLC of Formula: C8H6BrNO

Step A: 1-(2-Bromo-5-methoxyphenyl)methanamine 2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred overnight at rt, then quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.

According to the analysis of related databases, 138642-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); 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. 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methoxybenzonitrile

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8- methoxyphenanthridin-6-amine (0.95g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

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; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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-5-methoxybenzonitrile

Step A: KOH (4M, 259.66uL, 3.06eq) and Pd(Ph3P)2Cl2 (47.65mg, 67.88umol, 0.20eq) were added to a solutionof the intermediate 12 (200.00mg, 339.42umol, 1.00eq) and 2-bromo-5-methoxyphenyl cyanide (108.00mg, 509.13umol,1.50eq) in 2-methyltetrahydrofuran. The reaction solution was stirred at 65C under nitrogen atmosphere for 13 hours,then cooled to room temperature, and additional Pd(Ph3P)2Cl2 (20.00mg, 33umol, 0.10eq) was added. The reactionsolution was heated to 65C and stirred for another 3 hours to give 87, which was directly used in the next step. Thereaction solution was cooled to room temperature, then methanol (6.00mL) and water (3.00mL) were added and theresulting mixture was stirred at 35C for 2 hours. Lithium hydroxide (15mg) was added, the reaction solution was heatedto 45C and stirred for 3 hours. The reaction solution was cooled to room temperature, adjusted to pH 5 with 2M HCl,diluted with water, extract with ethyl acetate, dried over sodium sulfate, concentrated and purified by silica gel columnchromatography to give the intermediate 88.

The synthetic route of 2-Bromo-5-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.