Tag: M.W=200-300

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. 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrNO

16.23 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5.00 g of 5-bromo-2-methoxybenzonitrile in 90 ml of dry tetrahydrofuran at -78C. After stirring at this temperature for 45 minutes, 6.71 ml of triisopropylborate are added, and the mixture is then slowly warmed to -20C. 50 ml of 1 N HCl are added to the reaction mixture. The phase is separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, filtered and evaporated. The remaining oil is mixed with pentane, and the precipitate which separates out is filtered off with suction and washed once with a little dichloromethane. Drying under high vacuum affords the title compound as a white solid. Rt = 2.74.

According to the analysis of related databases, 144649-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Speedel Experimenta AG; EP1987834; (2008); A2;,
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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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 499983-13-0

Step 6: Preparation of 1 -(4-bromo-3-fluorophenyl)cyclopropanecarbonitrile; To a room temperature solution of (4-bromo-3-fluorophenyl)acetonitrile from Step 5 (6.4 g) in a solution of 7.5 mL of sodium hydroxide (50% in water WAV) were added l-bromo-2-chloroethane (4.0 mL) and benzyltriethylammonium chloride (204 mg). The mixture was heated at 600C for 5 hours. The reaction mixture was cooled to room temperature and poured into water (100 mL). The aqueous phase was extracted with ethyl acetate (200 mL). The combined organic extracts were washed with water (100 mL), hydrogen chloride (100 mL, 10% HCl in water) and brine and then dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using methyl t- butyl ether and hexanes to yield the title compound.1H NMR (CD3COCD3) delta 7.69-7.73 (1 H, m), 7.28 (1 H, d), 7.25 (1 H, d), 1.80-1.87 (2 H, m), 1.59-1.65 (2H, m).

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; MERCK FROSST CANADA LTD.; WO2006/133559; (2006); A1;,
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Related Products of 1813-33-8, 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. 1813-33-8 name is 2-Chloro-4-(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.

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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

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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Synthetic Route of 57381-37-0, 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. 57381-37-0 name is 2-Bromo-5-chlorobenzonitrile, 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.

A mixture of 5-chloro-2-bromobenzonitrile (107.5mg, 0.5mmol), cuprous oxide (36.0mg, 0.25mmol), cesium carbonate (489.3mg, 1.5mmol), methyl phenyl ketone (60.0mg, 0.5 after mmol) were added to a Schlenk reaction flask, vacuum, purged with nitrogen three times, in a nitrogen atmosphere, 10.0 mL of ethanol was added, the reaction 60 12 hours. after completion of the reaction, the solvent under reduced pressure, was removed by column chromatographic separation (elution with petroleum ether: ethyl acetate = 20: 1, V: V ), to give the product as a white solid 0.127g, 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Dalian University of Technology; BAO, MING; YU, XIAOQIANG; FENG, XIUJUAN; MOHAMMED, SHARIF MAYOU; WANG, JIAO; (18 pag.)CN104628643; (2016); B;,
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Reference of 79463-77-7,Some common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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.

Diphenyl cyanocarbonimidate (5.3 g, 21.56 mmol) in DCM (50 mL) was added to a sol. of l-(4methoxyphenyl)-2,2-dimethylpiperazine (5 g, 21.56 mmol) in DCM (190 mL). The r.m. was stirred at r.t. for 24 h. Water was added and the mixture was extracted with DCM. The separated organic layer was dried (MgS04), filtered and the solvent was evaporated. The residue was suspended in DIPE, filtered off and dried in the oven. Yield: 6.12 g of intermediate 1 (77 %).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2012/126984; (2012); A1;,
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Synthetic Route of 89642-49-9, A common heterocyclic compound, 89642-49-9, name is 4-Bromo-3-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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.

3.48. Compound 49: (lR,2R)-N-(6-(5-cyano-2-ethylphenylamino)-l-methyl-lH-imidazo[4,5- 3.48.1. Step i : 3-Nitro-4-vinyl-benzonitrile A mixture of 4-bromo-3-nitro-benzonitrile (1.0 eq, 1.0 g), potassium vinyl trifluoroborate (1.5 eq, 0.89 g), PdCl2(dppf).DCM (0.05 eq, 201 mg), K2C03 (3.0 eq, 1.82 g) in THF/water (10: 1; 20 mL) is heated at 80 C. After 1 h, the resulting mixture is diluted with DCM and aq. sat. NaHCOs, passed through a phase separator and concentrated. The residue is used as such in the next step.

The synthetic route of 89642-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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Related Products of 215800-25-2, 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. 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-bromo-3-methylphenylacetonitrile (1 g, 4.76 mmol) and methanol (10 mL) were added to a 25 mL singlemouth bottle, and thionyl chloride (5 mL) was added under ice bath. After reacted under ice bath for 20 minutes, the obtained mixture reacted at room temperature overnight. After completion of the reaction, the mixture was concentrated in vacuo to remove the solvent to give the product (colorless oil, 1 g), with a yield of 64.1%. 1H NMR (400 MHz, CDCl3) delta 7.47 (d, J = 8.1 Hz, 1H), 7.15 (s, 1H), 6.96 (dd, J= 8.2, 1.6 Hz, 1H), 3.69 (s, 3H), 3.55 (s, 2H), 2.38 (s, 3H).

The synthetic route of 2-(4-Bromo-3-methylphenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; YU, Fazhi; TANG, Ting; EP3476829; (2019); A1;,
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Related Products of 1813-33-8, The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

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

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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Reference of 425379-16-4, A common heterocyclic compound, 425379-16-4, name is 2-Bromo-3-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Step 3. 2′,6-Difluoro-5 ‘-(5 -(2-hydroxy- 1.1.1,3.3.3 – c -propan-2- ylV 1 H- benzo 1imidazol-l-yl biphenyl-2-carbonitrile (108): A mixture of lOu (1.7 g, 4.78 mmol), bis(pinacolato)diboron (1.47 g, 5.8 mmol) and KOAc (1.18 g, 12.0 mmol) in dioxane (30 mL) was purged with nitrogen for 5 minutes. Bis(triphenylphosphine)palladium(II)- dichloride (270 mg, 0.38 mmol) was added and the mixture was heated at 120 C overnight. The mixture was diluted with EtOAc (200 mL) and the solution was washed with water (2 x 30 mL) and brine, then dried (Na S04). After concentrating to dryness the material was dissolved in MeOH (30 mL) and concentrated to dryness again. The concentration step from MeOH was repeated a total of five times until about 2.1 g of a tan colored solid was obtained. This intermediate (2.1 g) was stirred in THF (20 mL) and water (10 mL) and was treated with 3-fluoro-2-bromo-l-cyanobenzene (1.2 g, 6 mmol) and K2C03 (1.5 g, 10.8 mmol). The mixture was purged with nitrogen for five minutes, then bis(di-t-butylphosphine) ferrocene palladium(II)dichloride (130 mg, 0.2 mmol) was added. The solution was heated at 60 C overnight. The cooled mixture was diluted with EtOAc (120 mL) and washed with water (30 mL). The organic phase was dried (Na2S04) and concentrated. The crude product was purified on an Analogix automated chromatography system eluting with 0-3% MeOH/CH2Cl2. The partially purified mixture was further purified on a reverse-phase CI 8 column eluting with 0-50% acetonitrile/water. The purest fractions were collected and concentrated to remove acetonitrile and the solid was isolated by filtration. This solid was passed through a short silica gel column eluting with 3% MeOH/CH2Cl2 to give 320 mg (17%) of 108 with 99.8% purity. 1H-NMR (300 MHz, CDC13): delta 1.89 (s, 1H), 7.42-7.44 (m, 0.19H), 7.45-7.47 (m, 0.65H), 7.47-7.50 (m, 0.76H), 7.51 (app d, J= 1.46, 0.33H), 7.53-7.67 (m, 6H), 7.99 (dd, J= 0.7, 1.7, 1H), 8.12 (s, 1H). 13C-NMR (75 MHz, CDC13): delta 109.95, 116.31, 117.79, 118.11, 120.75, 121.05, 121.32, 127.03, 127.15, 127.38, 129.32, 129.37, 131.15, 131.27, 132.53, 142.47, 143.92, 144.65, 158.05, 161.41. HPLC (method: Waters Atlantis T3 2.1 column 2.1 x 50 mm 3mu?iota – gradient method 5-95% ACN + 0.1% formic acid in 14 min with 4 min hold at 95% ACN+0.1% formic acid; wavelength: 305 nm):retention time: 5.85 min; 99.8% purity. MS (M+H): 396.3. Elemental Analysis(C^HnDgFa^O): Calculated: C=69.87, H=4.33, F=9.61, N=10.63. Found: C=79.27, H=4.05, F=9.63, N=10.53.

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; CONCERT PHARMACEUTICALS, INC.; LIU, Julie, F.; HARBESON, Scott, L.; WO2011/47315; (2011); A1;,
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Related Products of 20099-89-2, These common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, 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.

General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

Statistics shows that 4-(2-Bromoacetyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 20099-89-2.

Reference:
Article; Ma, Chunhua; Miao, Yuqi; Zhao, Minghao; Wu, Ping; Zhou, Jianglu; Li, Zhi; Xie, Xilei; Zhang, Wei; Tetrahedron; vol. 74; 27; (2018); p. 3602 – 3607;,
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