Category: 51632-29-2

Electric Literature of 51632-29-2,Some common heterocyclic compound, 51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, molecular formula is C14H11NO, 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.

EXAMPLE 1 284 g of 3-phenoxy benzyl cyanide and 220 g of di-ethyl oxalate were mixed and 400 ml of absolute ethanol was added. To this mixture was added gradually a solution of sodium ethoxide (prepared by dissolving 31 g of sodium in 410 ml of absolute ethanol). After the addition of the ethanol solution the mixture was warmed to 50 C for 30 minutes and then allowed to stand at room temperature for 12 hours. The reaction mixture was then acidified with ice-cooled 10% sulphuric acid (prepared by adding 37 ml of concentrated sulphuric acid to sufficient ice to give 370 ml of ice-cooled diluted acid). The product was extracted with methylene dichloride and the methylene dichloride solution was then washed neutral with distilled water. The product was dried over anhydrous sodium sulphate and the solvent removed. This product was treated with cold hexane to give ethyl 3-cyano-3-(3-phenoxyphenyl)-2-ketopropionate, melting point: 105-109, 90%. The structure was confirmed with proton magnetic resonance analysis (purity > 95%). The preparation of the cyanide from the bromide is illustrated in the following example.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Phenoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; Shell Oil Company; US4010190; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, belongs to nitriles-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. SDS of cas: 51632-29-2

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), deuterated dimethylamine borane complex (4 equivalents), potassium t-butoxide (2.5 equivalents), deuterated N,N-dimethylformamide (5 ml), added to the reaction tube After the rubber stopper was placed in an oil bath, the reaction was carried out at 100 C for 18 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. The eluent was petroleum ether/acetic acid B. Ester (v:v=10:1),Obtaining alpha-tridemethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25-ml two-neck round bottom flask was charged with alpha-tridemethyl-3-phenoxyphenylpropionitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml) in round bottomThe flask was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-tridemethyl-3-phenoxyphenylpropionic acid, alpha-tridemethyl-fenofol.Product yield 70%, light yellow solid

The synthetic route of 51632-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, 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. Formula: C14H11NO

1.38 g (6.59 mmol) of 3-phenoxyphenylacetonitrile and 1.57 g (6.59 mmol) of cobalt(II) chloride hexahydrate are dissolved in 25 ml of methanol. The solution is cooled with an iced water bath and 1.74 g (46 mmol) of sodium borohydride are added in portions. The reaction mixture is stirred overnight at ambient temperature. It is filtered on paper and rinsed with twice 25 ml of methanol. The filtrate is concentrated under reduced pressure and the residue is taken up in 50 ml of aqueous hydrochloric acid (1N) and 25 ml of ether. After distinct phases have separated out they are separated. The aqueous phase is washed with three times 25 ml of ether. The aqueous phase is rendered alkaline with 10 ml of aqueous 36% sodium hydroxide and extracted with three times 50 ml of dichloromethane. The extracts are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate and the filtrate is concentrated under reduced pressure. This gives 0.67 g of product in the form of a brown-orange oil, which is used as it is in the following step

The synthetic route of 2-(3-Phenoxyphenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, molecular formula is C14H11NO, 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. COA of Formula: C14H11NO

N-Methyl-2-(3-phenoxyphenyl)ethan-1-amine (I-52). Nitrile reduction: A round bottom flask was charged with nitrile I-51 (211 mg, 1 mmol, 1 eq), EtOH (5 mL) and 37% w/w aqueous HCl (0.16 mL, 2 mmol, 2 eq). N2 is bubbled through the solution for 5 minutes and Pd/C 10 wt.% (52 mg, 50 mumol, 5 mol%) is added. The mixture is sparged with N2 and then with H2 and is kept under H2 atmosphere (balloon). After 50 hours the reaction is complete as judged by TLC. The mixture is filtered over a Whatman filter and the filtrate is concentrated under reduced pressure to afford the product, which was used without further purification (246 mg, 0.98 mmol, 98%). TLC: Rf = 0.05 (6% MeOH/DCM). Carbamoylation: The carbamate was prepared according to general procedure C using amine (246 mg, 0.98 mmol, 1 eq), methylchloroformate (115 muL, 1.48 mmol, 1.5 eq) and DiPEA (517 muL, 3.0 mmol, 3 eq). Column chromatography (5% -> 40% EtOAc/pentane) afforded the product (176 mg, 0.65 mmol, 66%). TLC: Rf = 0.3 (10% EtOAc/pentane). Carbamate reduction: The title compound was prepared according to the general procedure D using carbamate (170 mg, 0.62 mmol, 1 eq), LiAlH4 (2 M THF solution, 0.52 mL, 1.04 mmol, 1.6 eq) and was used without further purification (125 mg, 0.55 mmol, 88%). TLC: Rf = 0.1 (6% MeOH/DCM).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51632-29-2, its application will become more common.

Synthetic Route of 51632-29-2, 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 51632-29-2 as follows.

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), dimethylamine borane complex (1 equivalent), potassium t-butoxide (1.5 eq.), deuterated N,N-dimethylformamide (2 ml), rubber stopper on the reaction tube After being placed in an oil bath, the reaction was carried out at 80 C for 7 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography, and the eluent was petroleum ether / ethyl acetate ( v: v = 10: 1), obtaining alpha-monodecylmethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25 ml two-neck round bottom flask was charged with alpha-monodeuteromethyl-3-phenoxyphenylpropanenitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml), burned in a round bottomThe bottle was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-monodecylmethyl-3-phenoxyphenylpropionic acid, i.e., alpha-monodecylmethyl-fenofol.Product yield 80%, light yellow solid

According to the analysis of related databases, 51632-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts