Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, 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 20099-89-2, Formula: C9H6BrNO

General procedure: A solution of 1a or 1b (0.001 mol) in acetone (10 mL), an appropriate substituted 2-bromoacetophenone derivative (0.001 mol) and potassium carbonate (0.138 g, 0.001 mol) were reuxed at 40 C for 12 h. The solvent was evaporated, residue was washed with water, dried and recrystallized from ethanol. The mass spectra of the compounds (3a-p) are available in the Supplementary Materials.

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, 4-(2-Bromoacetyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cevik, Ulviye Acar; Saglik, Beguem Nurpelin; Levent, Serkan; Osmaniye, Derya; Cavu?oglu, Betul Kaya; Ozkay, Yusuf; Kaplancikli, Zafer Asim; Molecules; vol. 24; 5; (2019);,
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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 134450-56-9 as follows. Application In Synthesis of 4,5-Difluorophthalonitrile

Compounds 5 and 6 were synthesized by reacting 4 with sub-stoichiometric or stoichiometric 4,5-difluorophthalonitrile, respectively, under basic conditions via nucleophilic aromatic substitution reaction. The targeted charged TADF emitters XI and XII were obtained following methylation with iodomethane and anion metathesis with saturated NH4PF6 solution in 33% and 27% yield, respectively, over six steps. The solubilities of XI and XII in DCM were greatly improved after the anion metathesis, in comparison with that of the original iodo salts.

According to the analysis of related databases, 134450-56-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; Zysman-Colman, Eli; Wong, Michael Yin; (41 pag.)US2017/352818; (2017); A1;,
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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 1009-35-4 as follows. SDS of cas: 1009-35-4

4-Fluoro-3-nitrobenzonitrile (182.6 g; 1.10 moles) was dissolved in DMF at 25- 30°C under nitrogen atmosphere and sodium carbonate (249.8 g; 2.36 moles) was added. The slurry was heated to 45-50°C and compound obtained in example- 05/DMF solution (327.12 g; 0.78 moles) was added in 30-60 min at 45-50°C. The reaction mass was maintained for ~8h at 45-50°C. After completion of the reaction by HPLC, reaction mass was diluted with ethyl acetate and water at < 50°C and stirred for 30-45 min. Layers were separated and aqueous layer was extracted with ethyl acetate. Combined organic layer was washed with -10percent w/v brine solution and concentrated under vacuum at < 55°C. Methanol was added to the concentrated residue and heated to 45-50°C and stirred for lh at 45-50°C. The obtained slurry was cooled to 25-30°C and maintained for lh at 25-30°C. The product was filtered and washed with methanol followed by water and then dried under vacuum to obtain the title product as a light yellow wet solid (369.2 g; 74.85percent of theory on dried basis). HPLC Purity: 95.91percent. According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular. Reference:
Patent; NATCO PHARMA LIMITED; APPAYE KALIYAPERUMAL, Srinivasan; TALASANI, Shyam Sunder Reddy; SAMATHAM, Nagalingam; KONDURI, Srinivasa Krishna Murthy; BUDIDETI, Shankar Reddy; MUDDASANI, Pulla Reddy; NANNAPANENI, Venkaiah Chowdary; (22 pag.)WO2019/38779; (2019); A1;,
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Application of 21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(3-Chlorophenyl)-3-oxopropanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
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Application of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

It was prepared as described for 8. Starting from 2-amino-6-fluorobenzonitrile (318 mg, 2.31 mmol) in 1,2-dichloroethane (25 mL) and enone 7 (R9 = i-Pr) (272 mg, 1.53 mmol) in 1,2-dichloroethane (15 mL), a crude product (383 mg) was obtained and subjected to column chromatography [silica gel (19 g), hexane/AcOEt/25% aqueous NH4OH mixtures as eluent]. On elution with hexane/AcOEt/25% aqueous NH4OH 98:2:0.1, huprine 10 (220 mg, 42% yield) was obtained as a beige solid.A solution of huprine 10 (220 mg, 0.74 mmol) in CH2Cl2 (15 mL) was filtered through a PTFE 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 30:1 (9.3 mL), 10·HCl (138 mg) was obtained as a beige solid, mp >300 C (dec.) (AcOEt/MeOH 30:1). IR (KBr) nu 3500-2500 (max at 3494, 3370, 3312, 3201, 3158, 3024, 2958, 2929, 2891, 2833, 2750, 2669, C-H, N-H, and N+-H st), 1640, 1595, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.87 (d, J = 7.0 Hz, 3H) and 0.89 (d, J = 7.0 Hz, 3 H) [9-CH(CH3)2], 1.97 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.02-2.12 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], superimposed in part 2.08 (br d, J = 17.5 Hz, 1H, 10-Hendo), 2.52 (br dd, J = 17.5 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.80 (m, 1H, 7-H), 2.86 (dm, J ? 18.0 Hz, 1H, 6-Hendo), 3.21 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.41 (m, 1H, 11-H), 4.85 (s, NH2 and NH+), 5.58 (dm, J = 5.0 Hz, 1H, 8-H), 7.34 (ddd, J = 13.5 Hz, J’ = 8.0 Hz, J = 1.0 Hz, 1H, 2-H), 7.56 (br d, J = 8.5 Hz, 1H, 4-H), 7.82 (dddm, J ? J’ ? 8.5 Hz, J = 5.5 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 27.2 (CH, C11), 27.9 (CH, C7), 29.6 (CH2, C13), 31.7 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 36.1 (CH2, C6), 107.2 (C, d, J ? 11.5 Hz, C12a), 112.2 (CH, d, J = 23.3 Hz, C2), 115.7 (C, C11a), 116.3 (CH, C4), 122.2 (CH, C8), 134.9 (CH, d, J ? 11.5 Hz, C3), 140.6 (C, C4a), 144.5 (C, C9), 152.9 (C) and 155.3 (C) (C5a and C12), 161.1 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H21FN2·HCl·3/4H2O (346.36): C, 65.89; H, 6.84; N, 8.09; Cl, 10.24. Found: C, 65.55; H, 6.62; N, 7.99; Cl, 10.21.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
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Reference of 3288-99-1, These common heterocyclic compound, 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)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.

In a 10 L-reaction flask equipped with a rectification column and a separating tank, 314 g (1.81 mol) of 4-tert-butylphenylacetonitrile, 300 g (1.65 mol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 3000 g of heptane, 225 g of diethylene glycol dimethyl ether, and 99 g of diethylene glycol monoethyl ether were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 381 g (1.98 mol) of 28% sodium methoxide methanol solution was added dropwise over 10 hours, and the resulting mixture was further reacted for 7 hours. After cooling to 30 C. or less, 3000 g of water was added to separate out heptane phase, and the resulting aqueous phase was further washed with 600 g of heptane to separate out heptane phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 466 g (yield 91.5%) of 2-(4-tert-butylphenyl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrile. After adding 2760 g of xylene to the aqueous phase, 206 g (1.98 mol) of 35% hydrochloric acid was added dropwise to be neutralized. After separating out the aqueous phase, the resulting organic phase was washed two times with 600 g of water and the aqueous phase was separated out to obtain xylene solution of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile. A quantitative analysis with liquid chromatography showed that the xylene solution contained 456 g (yield 89.6%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
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Reference of 2941-29-9, These common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, 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.

A mixture of 2-cyanocyclopentanone (20.0 g, 183 mmol, prepared as described in Fleming et al, J. Org. Chem. 2007, 72, 1431-1436 in the Supporting Information), water (24.7 ml), and sodium cyanide (14.8 g, 302 mmol) was cooled with an ice bath to a temperature of 5 °C to 10 °C. A mixture of sulfuric acid (29.3 ml, 550 mmol) and water (24.7 ml), said mixture having a temperature of 10 °C, was added drop wise within 0.5 h while stirring. The ice bath was then removed, and the mixture was stirred for 2.5 h at room temperature. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (3 x 100 ml). The combined extracts were dried with magnesium sulfate, and pyridine (51 ml, 631 mmol) was added. The solution was cooled with an ice bath to a temperature of 5 °C to 10 °C, and acetyl chloride (40.0 ml, 561 mmol) was added drop wise. The resulting mixture was stirred at 0 °C for 2 h, and then at room temperature overnight. After filtration and concentration under reduced pressure, toluene (100 ml) and ethyldiisopropylamine (94 ml, 553 mmol) were added to the residue, and the mixture was stirred at 100 °C for 6 h, and at room temperature overnight. The mixture was poured into a mixture of aqueous, concentrated hydrochloric acid (68 ml) and water (70 ml), phases were separated, the aqueous phase was extracted with ethyl acetate (3 x 150 ml), the combined extracts were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to yield 22.5 g of a dark oil. Distillation (2 mbar) yielded 8.6 g (40percent) of compound of formula (II) (bp 66-71 °C). 1H NMR (CDCls, 400 MHz) compound of formula (II): delta 2.17 (quint, J = 7 Hz, 2H), 2.83 (t, J = 7 Hz, 4H).

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONZA LTD; ZARAGOZA DOERWALD, Florencio; WO2013/102634; (2013); A1;,
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Application of 330793-38-9, 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. 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-(Methyoxy)-4-prop-2-en-l-ylbenzonitrile To a 50 mL flask containing a stir bar were added 2-methoxy-4-bromobenzonitrile (0.30 g, 1.4 mmol), palladium tetrakis (82 mg, 0.071 mmol), allyltri-n-butyltin (0.88 mL, 2.8 mmol), and lithium chloride (0.12 g, 2.8 mmol). The resulting mixture was then dissolved in anhydrous toluene (16 mL); the flask was placed in an oil bath and heated at 130 °C. LC as well as TLC (hexanes/EtOAc =1/0.3) indicated that reaction had gone to completion. The flask was taken out of the oil bath and cooled to room temperature. To the flask was added EtOAc (40 mL) and the mixture was transferred into a separatory funnel and washed with brine. The organic phase was dried over Na2S04, filtered and concentrated to dryness. It was then dissolved in DCM and absorbed into silica gel. The slica gel was then loaded onto a silica column for separation with the solvent systems of hexanes/EtOAc (1/0.3) to provide 2-(methyloxy)-4-prop-2-en-l- ylbenzonitrile. LC-MS (IE, m/z): 174 [M + 1]+.

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, 4-Bromo-2-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
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Application of 98730-77-9, 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. 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30 mmol, 2.36 g) in dichloromethane (30 mL) was treated with triethylamine (48.6 mmol, 6.83 mL, 4.92 g) and portionwise with methanesulfonyl chloride (31.6 mmol, 2.445 mL, 3.62 g) keeping the reaction mixture at 0 C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (*3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (1-cyanocyclopropyl)methyl methanesulfonate (3.77 g). 1H NMR (CDCL3, 400 MHz): delta 1.18 (2H, m), 1.46 (2H, m), 3.14 (3H, s), 4.18 (2H, s)

The chemical industry reduces the impact on the environment during synthesis 1-(Hydroxymethyl)cyclopropanecarbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); A1;,
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Electric Literature of 50397-74-5, 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. 50397-74-5 name is 4-Amino-3-bromobenzonitrile, 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.

An ethanolic solution (5 mL) of 4-amino-3-bromobenzonitrile (L3, 1 mmol, 0.197 g) was added to ethanolicsolution (5 mL) of AgNO3 (0.6 mmol, 0.1 g). The test tube was covered with a perforated foil. Afterkeeping the solution in air for 4 days, light yellow crystals of 3 suitable for structure determinationwere obtained. Yield 80%, m.p. 130-132 C. Anal. Calcd for C21H15AgBr3N7O3: C, 33.15; H, 1.99; N, 12.88%. Found: C, 33.14; H, 1.97; N, 12.89%. IR (KBr, cm-1): 3481 (m), 3360 (s), 3215 (w), 2628 (w), 2221 (s), 1769(w), 1633 (s), 1594 (m), 1507 (s), 1388 (s). 1H NMR (400 MHz, DMSO) delta/ppm: 7.83 (d, J = 1.9 Hz, 1H), 7.45(dd, J = 8.5, 1.9 Hz, 1H), 6.82 (d, J = 8.5 Hz, 1H), 6.37 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Qian, Wei; Yuan, Hao-Kun; Zhang, Ran; Fang, Rui-Qin; Journal of Coordination Chemistry; vol. 69; 23; (2016); p. 3593 – 3602;,
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