Tag: M.W=100-200

These common heterocyclic compound, 698-01-1, name is 2-Chloro-N,N-dimethylaniline, 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. Application In Synthesis of 2-Chloro-N,N-dimethylaniline

General procedure: In to an oven-dried flask, N,N-dimethylaniline 1a(2.0 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene 2a (1.0mmol), CuCl (0.2 mmol), PPh3 (0.4 mmol), SDS (0.5 mmol) and TBHP (70wt% aqueous, 2.7 mmol) were added at room temperature. In open air, water (5mL) was added and the reaction mixture was allowed to reaction at 70 oCfor 6 h. After the finish of the reaction, the mixture was filtered through apad of celite and the filtrate was extracted by EA three times. The combined organic layers was washed by brine and dried by Na2SO4. Afterthe removing of the organic solvents, the residue was then separated on a silica gel column and the final product was obtained as a yellow powder (174 mg, 52%).

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

Reference:
Article; Xie, Chunsong; Han, Laihong; Tetrahedron Letters; vol. 55; 1; (2014); p. 240 – 243;,
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Electric Literature of 1435-48-9, The chemical industry reduces the impact on the environment during synthesis 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 60 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-thienyl-1-piperazinyl]-3-quinolinecarboxylic acid A mixture of 229.6 g of 1,3-dichloro-4-fluorobenzene and 205.34 g of aluminum chloride was heated at 80 C. A 56 g portion of acetic anhydride was added dropwise over 2 hours, then the reaction was heated at 100 C. for 8 hours, poured onto a mixture of concentrated hydrochloric acid and ice and extracted several times with ether. The ether extracts were combined, washed with water, dried and the solvents evaporated. The solid was purified by vacuum distillation, giving 156.63 g of 6-acetyl-1,3-dichloro-4-fluorobenzene.

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, 2,4-Dichloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Cyanamid Company; US4940710; (1990); A;,
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Related Products of 261762-56-5, 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 5-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-([methylsulfanyl]methyl)propyl]amino}-1H-quinolin-2-one2-Chloro-3-fluoro-4-methoxybenzaldehyde; 1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After one hour at -70 3.93 ml DMF in 7 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

The synthetic route of 1-Chloro-2-fluoro-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); A1;,
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Reference of 7781-10-4,Some common heterocyclic compound, 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C7H6ClN3, 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 part of the resulted N-methylated compound (500 mg, 2.98 mmol) was dissolved in 5 ml abs. THF and cooled down to -78 C. Then 2M LDA (1.7 ml, 3.4 mmol) was added dropwise. The mixture was stirred at -78C for 1 hour, then iodide (757 mg, 2.98 mmol)was added. The solution was allowed to warm to r.t. and stirred for 22 hours, then 5 mlwater was added. Solid compound was formed and filtered off to give Preparation R2aj.HRMS calculated for C7H61N30: 274.9556; found 275.9634 [(M+H)+ form].1H-NMR(500 MHz, dmso-d6) oe ppm 11.97 (s, 1 H), 7.85 (s, 1 H), 6.79 (s, 1 H), 3.64 (s, 3H)13C-NMR(500 MHz, dmso-d6) oe ppm 157.3, 149.1, 144.2, 111.4, 110.3, 80.4, 33.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, its application will become more common.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; WEBER, Csaba; VASAS, Attila; MOLNAR, Balazs; KISS, Arpad; MACIAS, Alba; MURRAY, James Brooke; LEWKOWICZ, Elodie; GENESTE, Olivier; CHANRION, Maia; DEMARLES, Didier; (105 pag.)WO2017/212012; (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 106-39-8 as follows. Quality Control of 1-Bromo-4-chlorobenzene

General procedure: A flame-dried 50mL round-bottom flask equipped with amagnetic stir bar and a rubber septum was charged with arylhalide (1.0mmol), phenyl boronic acid (1.1mmol), K2CO3(2.0mmol) and CL-salen-Pd(II) (0.5% mmol). The mixturewas stirred in Ethanol: H2O= 1:1 (5.0mL) at 50 underair atmosphere for 1h. The mixture was cooled to roomtemperature, quenched with water (5mL), and diluted withethyl acetate (5mL). The layers were separated, and theaqueous layer was extracted with 2 × 5mL of ethyl acetate.The combined organic extracts were dried over anhydrousmagnesium sulfate, filtered, and concentrated in vacuo.Finally, the product was purified by column chromatography.

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Chunxia; Peng, Jinsong; Sun, Peng; Xie, Kaijun; Yang, Jiaojiao; Catalysis Letters; (2020);,
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Reference of 2845-89-8, These common heterocyclic compound, 2845-89-8, name is 1-Chloro-3-methoxybenzene, 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.

Unless special limited, generally the reaction conditions are as follows: 110 C lower, aryl chloride (0.7mmol), the secondary amine (1.2equiv. , Relative to the aryl chloride), the tertiary butyl alcohol potassium (1.3equiv. , Relative to the aryl chloride), complex (41) (0.02 muM %) (40muL, complex (41) (9.7 mg) dissolved in 4.0 ml of 1, 4 – dioxane), 1, 4 – dioxane (1.0 ml) the reaction 24 hours. Yield rate of the product after separation and purification.

Statistics shows that 1-Chloro-3-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 2845-89-8.

Reference:
Patent; Wenzhou University; Shao Lixiong; Lu Jianmei; Liu Feng; (23 pag.)CN106892945; (2017); 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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7ClFN

(i) [1-(Triphenylmethyl)-1H-pyrazol-4-yl]acetic acid (0.460 g, 1.25 mmol, which can be prepared as described in WO 95/07283) was dissolved in dichloromethane (30 ml) and to this was added water soluble carbodiimide (0.312 g, 1.63 mmol), 1- hydroxybenzotriazole (0.220 g, 1.63 mmol), N-ethyl morpholine (0.477 ml, 3.75 mmol), and [(2-chloro-4-fluorophenyl)methyl]amine (0.209 ml, 1.63 mmol). The mixture was stirred at room temperature under argon for 18 hours and then diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate. The mixture was then filtered through a hydrophobic frit and the organic phase was evaporated to give the crude product as a yellow oil. The crude material was purified by automated (Biotage SP4) flash-silica column chromatography, eluting with 0-80% ethyl acetate in hexane to give lambda/-[(2-chloro-4-fluorophenyl)methyl]-2-[1- (triphenylmethyl)-1 H-pyrazol-4-yl]acetamide as a white solid (0.330 g). LC/MS [M+H]+ = n.d., retention time = 3.64 minutes

The synthetic route of 15205-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/138876; (2008); A1;,
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Reference of 694-80-4, These common heterocyclic compound, 694-80-4, name is 1-Bromo-2-chlorobenzene, 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.

Add to Schlenk tubeN- (2-mercapto) acetamide(0.3 mmol, 50.1 mg), FeSO47H2O (0.06 mmol, 16.68 mg),1,10-lindolinol (0.06 mmol, 10.8 mg) andPotassium tert-butoxide (1.2 mmol, 134.4 mg)With nitrogen to protect the reaction system (pumping gas three times),1,2-dibromobenzene (0.45 mmol, 105.2 mg) and DMF (2 mL) were added to the reaction system with a syringe,Heated to 135 C,Stirring reaction 24hAfter completion of the reaction, the mixture was cooled to room temperature,20 mL of water was added and extracted three times with ether,The organic phase was washed with water, dried over anhydrous sodium sulfate,Column chromatography to obtain the product10H-phenothiazine. Yield 70%.Using a method similar to that of Example 1,Respectively, with o-bromobenzene,O-bromochlorobenzene,O-chlorobenzene,O-dichlorobenzene was used in place of o-dibromobenzene in Example 1 to give the product phenothiazine in a yield of 72%, 81%80%, 20%.

Statistics shows that 1-Bromo-2-chlorobenzene is playing an increasingly important role. we look forward to future research findings about 694-80-4.

Reference:
Patent; Suzhou University; Zhang, Songlin; Hu, Weiye; Zheng, Songlin; Wu, San; Wang, Ru; Zhang, Fang; (7 pag.)CN104311508; (2017); B;,
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Synthetic Route of 2106-02-7,Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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.

Into a 20-L 4-neck round flask was placed a solution of2-chloro-4-fluorobenzenamine (1300 g, 8.82 mol, 1.00 equiv, 99%) in toluene (10 L), 4-methylbenzenesulfonic acid (3.1 g, 17.84 mmol, 99%), and hexane-2,5-dione (1222.5 g, 10.62 mol, 1.20 equiv, 99%). The resulting solution was heated to reflux for 1 h in an oil bath and cooled. The pH value of the solution was adjusted to 8 with sodium carbonate (1 mol/L). The resulting mixture was washed with 1×5000 mL of water and concentrated under vacuum. The crude product was purified by distillation and the fraction was collected at 140 0C to afford l-(2-chloro-4-fluorophenyl)-2,5-dimethyl-lH-pyrrole (1700 g, yield: 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-fluoroaniline, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; PULK, Rebecca; RUDOLPH, Joachim; WEN, Zhaoyang; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25940; (2011); A1;,
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Application of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 suspension of 3-bromo-4-fluoro-5-nitrobenzoic acid (24b, 150 mg, 0.568 mmol) in SOCl2 (2 mL) was stirred at 60 C. for 3 hours. The mixture was concentrated to obtain 3-bromo-4-fluoro-5-nitro-benzoyl chloride (214 mg, crude) as a white solid. To a mixture of 4-(chlorodifluoromethoxy)aniline (1h, 146.64 mg, 0.758 mmol) and pyridine (89.89 mg, 1.13 mmol, 91.72 uL) in THF (2 mL) under N2 was added 3-bromo-4-fluoro-5-nitro-benzoyl chloride (213.97 mg, 0.758 mmol). The mixture was stirred at 20 C. for 3 hours. LCMS showed the desired MS. The mixture was extracted with ethyl acetate (2 mL*3), the combined organic layers were washed with brine (5 mL*2), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (SiO2, petroleum ether:ethyl acetate=1: 1, Rf=0.3). Compound 24c was obtained as a white solid.

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
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