Author: Jessica.F

Some common heterocyclic compound, 53005-44-0, name is 2-Methoxy-6-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. Recommanded Product: 53005-44-0

To intermediate 145 (5.0 g, 34.03 mmol) in THF (50 ml), benzylmagnesium chloride (34 ml, 2M in THF, 68.02 mmol) was added at 0C over 30 min. and heated to reflux for 15 h. The reaction mixture was cooled to room temperature, 2N HC1 (200 ml) was added and again refluxed for 4h. The reaction mixture was cooled and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford to afford the title compound as brown liquid (3.7 g , 45%). -NMR (delta ppm, CDCI3, 400 MHz): 7.30-7. 18 (m, 6H), 6.76 (m, 2H), 4.07 (s, 2H), 3.83 (s, 3H), 2.02 (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 53005-44-0, its application will become more common.

Reference:
Patent; RHIZEN PHARMACEUTICALS SA; NAGARATHNAM, Dhanapalan; VAKKALANKA, Swaroop Kumar, V.S.; MUTHUPPALANIAPPAN, Meyyappan; VISWANADHA, Srikant; BABU, Govindarajulu; BHAVAR, Prashant, Kashinath; WO2012/151525; (2012); A1;,
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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. 3100-67-2, name is 1-Amino-2-naphthonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Amino-2-naphthonitrile

A solution of [Intermediate 7-a] (18.5 g, 0.11 mol) in dimethyl formamide (200 mL) was stirred at 0 C. Drops of a solution of N-bromosuccinimide (20.1 g, 0.11 mol) in dimethyl formamide (100 mL) were slowly added over 1 hr. The reaction mixture was warmed to room temperature and stirred for 12 hrs. Following filtration with an excess of distilled water, the filtrate was washed with methanol and recrystallized in toluene and methanol to afford [Intermediate 7-b] (18.7 g): yield 69%.

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; SFC CO., LTD.; LEE, Chang-Hee; SEO, Hyun-JONG; YOON, Seo-Yeon; SHIM, So Young; KIM, Si-In; (214 pag.)US2018/233669; (2018); A1;,
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Reference of 874285-03-7,Some common heterocyclic compound, 874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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.

2-(3-bromo-2-fluorophenyl)acetonitrile (800 mg, 3.7 mmol,1 eq.) and (S)-1- iodo-2-(2-iodoethoxy)propane (1.27 g, 3.74 mmol, 1 eq.) were dissolved in dimethyl sulfoxide (10 ml_). Sodium hydride (331 mg, 8.3 mmol, 2.2 eq.) was added to the reaction mixture and stirred for 1 h at room temperature. The reaction mixture was diluted with water (10 ml_) and ethyl acetate (10 ml_), and the layers were separated. The organic phase was washed with 1 M HCI (1×10 ml_), water (1×10 ml_) and brine (1×10 ml_). The organic phase was concentrated under vacuum to afford a diastereomehc mixture of (2S,4R)-4- (3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2H-pyran-4-carbonitrile and (2S,4S)-4-(3-bromo-2-fluorophenyl)-2-methyl-tetrahydro-2/-/-pyran-4- carbonitrile (1 :1 ). The diastereomehc mixture was separated by reverse phase chromatography (40 – 90% acetonithle-water) to obtain the title compound (252 mg, 23%) as a single isomer. Stereochemistry confirmed by NMR. [2SAR)- 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.26 (d, J=6.2 Hz, 3 H) 1.81 (dd, J=13.2, 11.0 Hz, 1 H) 2.08 – 2.26 (m, 3 H) 3.89 – 4.02 (m, 2H) 4.04 – 4.16 (m, 1 H) 6.99 – 7.13 (m, 1 H) 7.32-7.44 (m, 1 H) (s, 1 H) 7.51 – 7.63 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%). (2S,4S): 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 1.22 (d, J=6.2 Hz, 3 H) 2.05 (dd, J=14.5, 10.7 Hz, 1 H) 2.25-2.44 (m, 1 H) 2.49 – 2.63 (m, 2 H) 3.44 – 3.59 (m, 2H) 3.86 – 3.99 (m, 1 H) 7.02 – 7.13 (m, 1 H) 7.19-7.31 (m, 1 H) (s, 1 H) 7.53-7.64 (m, 1 H); LC/MS (M+H) = 298 (100%), 300 (98.5%).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
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Reference of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 solution of the corresponding aryl fluoride (0.2 mmol) and the corresponding alcohol (0.200 mmol) in DMF (1 mL) is added 0.5 mL of 0.6 M slurry of sodium hydride (60%) in DMF (0.3 mmol). The resultant mixtures were shaken at room temperature for 48 hours. The reactions were quenched with water (0.5 mL). The solvent is evaporated in vacuo. To the concentrated reaction mixtures is added methylene chloride (3 mL) and water (2 mL). The organic layer is filtered through silica (0.5 g) solid phase extraction column and evaporated to yield material that was purified by reverse phase HPLC.

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; Pfizer Inc; US2009/170886; (2009); A1;,
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Reference of 867367-02-0, 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. 867367-02-0, name is 4-Fluoro-3,5-dimethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-[4-Chloro-3-(4-cyano-2,6-dimethyl-phenoxy)-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-55) step 1-A solution of 40 (0.600 g, 2.79 mmol), 3,5-dimethyl4-fluorobenzonitrile (41, 0.459 g, 3.07 mmol), K2CO3 (1.157 g, 8.37 mmol) and NMP (6 mL) was stirred and heated to 120 C. for 6 h. When the starting material was consumed the solution was cooled and acidified with 10% HCl and twice extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography and eluted with an EtOAc/hexane gradient (100% hexane to 50% hexane) to afford 106a. Steps 2-4 were carried out as described in steps 7-9 of Example 1 which afforded I-55. Compound I-56 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-methyl-benzenesulfonamide. Compound I-68 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 2-chloroaniline. Compound I-135 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-chloro-benzenesulfonamide.

The synthetic route of 4-Fluoro-3,5-dimethylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); A1;,
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Synthetic Route of 129931-47-1, 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. 129931-47-1 name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, 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.

(g) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-trifluoromethyl-2-pyridone (Compound No 14 of Table II) was prepared by reacting 3-chloro-4-fluoro-5-cyanotrifluoromethylbenzene and 4-trifluoromethyl-2-pyridone. 1 H NMR delta(CDCl3) 8.10 (1H,d); 8.0 (1H,d); 7.26 (1H,dd); 7.04 (1H,s); 6.55 (1H,dd).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
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Reference of 100-47-0, 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 100-47-0 as follows.

Example 1: o-trifluoromethylbenzonitrile. Dark at room temperature, the appropriate amount of the organic solvent (a mixed solvent of acetonitrile and DMSO, both the volume ratio of 1: 0.3) was added 100mmol compound of formula (II), the compound of 150mmol of formula (III), 2 mmol methylbenzene and triazole silver and 200mmol potassium t-butoxide, raising the temperature to 30 , and stirred for 30 minutes, then added dibenzo-18-crown-6, heated to 70 and the reaction was kept stirring for 5 hours; After completion of the reaction, the reaction mixture was added to 1 volume of its diluted with ethyl acetate, and washed successively with saturated aqueous sodium bicarbonate solution, and saturated brine, the organic phase was separated, which was dried over anhydrous sodium sulfate and evaporated distillation, the residue was subjected to silica gel column chromatography (eluent of ethyl acetate and n-butanol mixed solvent, a volume ratio of between 2: 1) to give the compound of the nitrile o-trifluoromethylbenzene of formula (I) (the ortho product yield 92.5%).

According to the analysis of related databases, 100-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujian Wanke Pharmaceutical Co., Ltd; Li, yibiao; Pan, MeiLing; Pan, meixia; (9 pag.)CN104649934; (2016); B;,
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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 619-72-7 as follows. Recommanded Product: 4-Nitrobenzonitrile

General procedure: Photocatalytic reactions were carried out in a round bottom Pyrex flask and irradiated using four high power blue light LEDs 3W lamp or by solar light under magnetic stirring at room temperature. Reaction conditions with solar light: the aromatic nitro compounds (0.05mmol) and anhydride (0.052mmol) were carried out in the presence of TiO2-P25 (0.03g) in EtOH (10mL) and irradiated under sunlight for 1-4 h. Reaction conditions with blue LED irradiation: aromatic nitro compounds (0.002mmol) and anhydride (0.0025mmol) were carried out in the presence of TiO2-P25 (0.08g) in EtOH (4mL), and irradiated by four high power blue light LEDs 3W lamp for 30 h. While stirring, the mixture became heterogeneous as the reaction progressed. The product yields were determined by gas chromatography monitoring. The structure of products were confirmed by NMR (see ESI1).

According to the analysis of related databases, 619-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zand, Zahra; Kazemi, Foad; Partovi, Adel; Journal of Photochemistry and Photobiology B: Biology; vol. 152; (2015); p. 58 – 62;,
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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. 2856-63-5, name is 2-(2-Chlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2856-63-5

Example 30 Synthesis of 2-cyanomethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (92%) of the title compound.

The synthetic route of 2856-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buchwald, Stephen L.; Huang, Xiaohua; Zim, Danilo; US2004/171833; (2004); A1;,
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Synthetic Route of 1528-41-2, 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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 50 ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate [0235] Combined ethyl 2-(4-cyanophenyl)acetate (25 g, 0.132 mol) with DMF-DEA (60 mL) and heated to 70C for 3 hours. The reaction mixture was cooled to room temperature and concentrated and then purified by flash chromatography to give the title compound (20 g, 62%) as a solid. XH NMR (400 MHz, DMSO-i) delta ppm 7.71 (d, J=8.4Hz, 2H), 7.59 (s, 1H), 7.29 (d, J=8.4Hz, 2H), 4.03 (q, J=6.8Hz, 2H), 2.67 (s, 6H), 1.13 (t, J=6.8Hz, 3H).

The synthetic route of Ethyl 2-(4-cyanophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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