Category: 3556-60-3

Synthetic Route of 3556-60-3,Some common heterocyclic compound, 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, molecular formula is C9H9NO, 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.

C.14.e. 4-Bromomethyl-3-methoxybenzonitrile 14.7 g (0.1 mol) of 3-methoxy-4-methylbenzonitrile were dissolved in 210 ml of 1,2-dichloroethane, brominated in portions with 19.1 g (0.11 mol) with NBS over the course of 1 h in the presence of catalytic amounts of AIBN at 82 C. and, after the addition was complete, stirred at 82 C. for a further 30 min. After addition of n-heptane, precipitated succinimide was removed, and the solvent was stripped off. The product contained traces of the corresponding benzal bromide in addition to small amounts of precursor. 1H-NMR (DMSO-d6; delta in ppm): 7.60 (dd, 1H); 7.50 (d, 1H); 7.40 (dd, 1H); 4.68 (s, 2H); 3.96 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6455671; (2002); B1;,
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Nitriles – Chemistry LibreTexts

Application of 3556-60-3, 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. 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an inert atmosphere, to a solution of 3-methoxy-4-methylbenzonitrile (2.00 g, 13.6 mmol) in tetrahydrofuran (50 mL), a methylmagnesium chloride solution (5 mL, 3M in tetrahydrofuran) was added dropwise during cooling with ice at 0-2 C, and the mixture was stirred at 40 C for 12 hours. (0195) The reaction mixture was quenched by dropwise addition of 6 M HC1 solution (3.4 mL), and was stirred stirred at 40 C for another hour. The mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over Na?.S04, evaporated, and the crude residue was purified with column chromatography on silica gel with gradient elution, using a mixture of dichlorom ethane and cyclohexane as eluent. Yield: 356 mg (16 %).

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

Reference:
Patent; RICHTER GEDEON NYRT.; LEDNECZKI, Istvan; ELES, Janos; TAPOLCSANYI, Pal; JABLONKAI, Erszebet; GABOR, Eszter; VISEGRADI, Andras; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; PETRO, Jozsef Levente; SELENYI, Gyoergy; (0 pag.)WO2020/12423; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 3556-60-3,Some common heterocyclic compound, 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, molecular formula is C9H9NO, 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-methoxy-4-methylbenzonitrile (300 mg, 2.03 mmol) in 10 ml ethanol was added hydroxylammonium chloride (212 mg, 3.06 mmol) and triethylamine (268 mg, 2.65 mmol) and then the reaction mixture was stirred overnight at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and extracted with water and brine solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (274 mg, 75 % of theory). LC-MS (method IB): RT = 0.33 min, m/z = 181 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 3556-60-3

A mixture of 3-methoxy-4-methylbenzonitrile (3.5 g, 24 mmol), NBS (4.4 g, 25 mmol), and AIBN (0.39 g, 2.4 mmol) in benzene (240 mL) under nitrogen was heated at 85 C for 18 h, then cooled and concentrated. The residue was purified by silica gel chromatography (hexanes initially, grading to 50% EtOAc in hexanes) to give the title compound. MS: mlz = 226.0 [M+l]+.

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Reference:
Patent; MERCK SHARP & DOHME CORP.; CROWLEY, Brendan; FRALEY, Mark; POTTEIGER, Craig; LIM, John; SHERER, Ed; YU, Younong; MITCHELL, Helen; BIFTU, Tesfaye; NAIR, Anilkumar; WANG, Cheng; YANG, De-Yi; ZHU, Cheng; KAR, Nam Fung; HUANG, Xianhai; CHEN, Lei; ZHOU, Wei; PARK, Min, K.; CAI, Jiaqiang; WO2015/161014; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts