Tag: M.W=200-300

1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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: 1813-33-8

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. SDS of cas: 154607-01-9

3-Chloro-2′,4′-difluorobiphenyl-4-carbonitrile (EM-4283): In a round bottom flask, 4-bromo-2-chlorobenzonitrile (3 g, 13.85 mmol), 2,4-difluorophenylboronic acid (2.63 g, 16.63 mmol) and K3PO4 (8.83 g, 41.56 mmol) were added in dry DMF (50 mL). The mixture was purged under argon for 30 min and Pd(PPh3)4 (1.6 g, 1.38 mmol) was added. The mixture was heated for 48 hr at 80 C. Water (100 mL) was added and the aq layer was extracted with CH2Cl2(3*50 mL). The organic layer was washed with brine (3*50 mL), dried, evaporated and purified on silica gel (EtOAc/hexanes:1/19) to give the product (1 g, 29%), 1H.NMR (acetone-d6) delta: 7.2-7.28 (m, 2H), 7.72-7.79 (m, 2H), 7.91 (t, 1H, J=1.4 Hz), 8.02 (d, 1H, J=8.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 154607-01-9, its application will become more common.

Reference:
Patent; Endorecherche, Inc.; US2004/6134; (2004); A1;,
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These common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

A flask which had been dried by heating and flushed with argon was initially charged with 1.0 eq. of the appropriate boronic acids, 1.0 eq. of the aryl bromide or aryl iodide, 3.0 eq. of potassium carbonate and 0.1 eq. of [1,1 -bis(diphenylphosphino)ferrocenelpalladium(II) chloride/monodichloromethane adduct or tetrakis(triphenylphosphine)palladium(0). The flask was then evacuated three times and in each case vented with argon. Dioxane (about 6 ml/mmol) was added, and the reaction mixture was stirred at 110 C. for a number of hours until substantially complete conversion had been achieved. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water and once with saturated aqueous sodium chloride solution, dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified either by means of normal phase chromatography (cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient).

The synthetic route of 2-Bromo-4-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; US2018/346424; (2018); A1;,
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Related Products of 79463-77-7, 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 79463-77-7 as follows.

A mixture of 3-aminobenzotrifluoride (15 g, 93 mmol) and diphenyl cyanocarbon-imidate (22.2 g, 93 mmol) was heated at reflux in THF (100 ml) for 20 h. The r.m. was then concentrated under reduced pressure. H2O was then added and the resulting solid was filtered and dried in vacuo, yielding 20.7 g of intermediate 35 (72%).

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
Nitrile – Wikipedia,
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Electric Literature of 4592-94-3, 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. 4592-94-3 name is 3-(4-Bromophenyl)-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: To the 1 mol eq. of 3-aryl-3-oxopropanonitrile (2) was added1 mol eq. of hydrazine hydrate (1) in Toluene/EtOH (9:1) and thereaction mixture was refluxed for 30 min then another 1 mol eq. ofdifferent 3-aryl-3-oxopropanonitrile (2) and catalytic amount ofPTSA (0.01 mol eq.) was added. Again reaction mixture wasrefluxed up to 4 h. On completion of the reaction, excess solvent was distilled off. The solid so obtained was filtered and washedwith cold ethanol. Solid was neutralised with aq. sodium bicarbonatesolution and again filtered. Compound thus obtained wasair dried and recrystallized from ethanol.

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

Reference:
Article; Aggarwal, Ranjana; Singh, Gulshan; Kaushik, Pawan; Kaushik, Dhirender; Paliwal, Deepika; Kumar, Ajay; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 326 – 333;,
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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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1813-33-8

EXAMPLE 17 1′-[4-[1-(4-Fluorophenyl)-5-trifluoromethylindazol-3-yl]-1-butyl]spiro]isobenzofuran-1(3H),4′-piperidine], 17a. To a suspension of magnesium turnings (135 g) in 300 ml of dry tetrahydrofuran, ethyl bromide (140 g) dissolved in 500 ml of dry tetrahydrofuran was slowly added followed by reflux for 20 min. A solution of 4-chloro-1-butanol (274 g) in 500 ml of tetrahydrofuran was added dropwise at reflux temperature. After stirring for 20 min, the Grignard solution was filtered and added portionwise to a solution of 2-chloro-4-trifluoromethyl-benzonitril (200 g) in 600 ml of dry tetrahydrofuran. The reaction mixture was stirred for 16 h at room temperature followed by addition af 2N hydrochloric acid and ice. Extraction with ether, drying of the ether phase over magnesium sulfate and removal of solvent in vacuo left a viscous oil which was applied to a silica gel column (eluent:dichloromethane/ether=3:1) giving 4-(2-chloro-5-trifluoromethylbenzoyl)-1-butanol (101 g) as an oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1813-33-8.

Reference:
Patent; Lundbeck; H.; US5665725; (1997); A;,
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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. 185836-35-5, name is 4-(Benzyloxy)-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 185836-35-5

A solution of [(R)- (-)-L-AMINO-PROPAN-2-OL] (389 g, 5.19 mol) in dimethyl sulfoxide (600 mL) was added to a solution of the product from Step A (786 g, 3.46 mol), basic alumina (786 g), and [4A] molecular sieves (131 g). The stirred mixture was heated at 110- 140 oC for 24 h, cooled and filtered, the filter-aide was washed with 10 L of 4: 1 ether- ethyl acetate followed by 4 L of 3: 2 ethyl acetate-hexane. The organic washes were extracted with water (5 L) and the aqueous phase was extracted with 25% ethyl acetate- hexane (4 x 2 L). The combined organic phases were washed with water and brine, dried over sodium sulfate, concentrated to about 3 L and allowed to stand for 48 h. The precipitated solid was collected by filtration, washed with hexane, and vacuum-dried to provide the desired product in two crops (619 g and 86 g). The concentated supernatant was applied to a 5 kg silica gel pad and eluted with a gradient of 10-50% ethyl acetate- hexane to give, after concentration in vacuo, additional product (119 g): total yield was 791 g [(8 1 %).]

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; ALCON, INC.; WO2003/101379; (2003); A2;,
Nitrile – Wikipedia,
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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. 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 120315-65-3

0.18 mmol intermediate example 2.1 (0.45 mL, 0.4M in NMP), 0.15 mmol 4-Bromo-3-methoxybenzonitrile (1.44 mL, 0.5M in NMP, 4 eq), 0.018 mmol Pd2(dba)3 (0.180 mL, 0.1M in NMP, 0.1 eq), 0.036 mmol rac-BINAP (0.180 mL, 0.1M in NMP, 0.2 eq) and 0.3 mmol NaOtBu (0.188 mL, 1.6M in water, 3 eq) were combined in a sealed vial and heated at 170 C under microwave irradiation for 45 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 12.0 mg (17 %) 4-{[6-(4-hydroxy-3,5-dimethylphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}-3-methoxybenzonitrile: 1H-NMR (300 MHz, d6-DMSO): delta = 9.00 (1 H, s), 9.02 (1 H, s), 8.61 (1 H, s), 8.42 (1 H, d), 8.41 (1 H, s), 7.88 (1 H, d) 7.62 (1 H, d), 7.43 (1 H, d), 7.40 (1H, s), 7.33 (2H, s), 3.90 (3H, s), 2.20 (6H, s) ppm. UPLC-MS: RT = 1.23 min; m/z (ES+) 386.4 [MH+]; required MW = 385.4.

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; Bayer Schering Pharma AG; EP2343295; (2011); 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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-3-fluorophenylacetonitrile

General procedure: To a solution of 3-fluoro-4-bromophenylacetonitrile (2g, 9.2mmol) and 1,2-dibromoethane (0.6ml, 7mmol) in toluene (5ml) was added 50% NaOH (5mL) and TBAB (0.32g , 1 mmol). The mixture was stirred vigorously at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate.The organic solution was washed with 1N HCl and then with brine, dried over anhydrous sodium sulfate and concentrated.Separation by column chromatography (eluent: PE / EA = 20/1, v / v), a yellow solid was obtained with a yield of 91%.

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; He Siyu; Liu Yang; (25 pag.)CN110590548; (2019); A;,
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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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H3ClF3N

To a flask was added Pd2dba3 (0.405 g), DavePhos (0.6884 g, 1.75 mmol), and CuI (0.1655 g). This was purged with nitrogen and degassed; triethylamine (100 mL) was then added. Benzonitrile (XVII) (36.2 g, 176 mmol) was then added, and the mixture was heated to 65 0C. 3,3-dimethylbutyne (23.7 g, 288 mmol) was then slowly added over 2 hours. The mixture was heated an additional 2 hours, and the heat removed. The mixture was diluted with isopropyl acetate (150 mL) and washed twice with water (150 mL) and twice with 10% aqueous citric acid (150 mL). The organics were diluted with methanol (40 mL), and the volume reduced in vacuo to 60 mL. This was repeated twice with 190 mL methanol, the residual material diluted to 250 g with methanol and used in the next step as a solution. An analytical sample was obtained by removing all the solvent in vacuo.1H NMR (CDCl3, 400 mHz) 7.75 – 7.70 (m, 2H), 7.60-7.55 (m, IH), 1.37 (s, 9H); 13C NMR (CDCl3, 100MHz) 132.6, 128.7, 128.6, 123.8, 123.7, 116.24, 107.96, 75.06, 30.73, 28.64.

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/117626; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts