Author: Jessica.F

Synthetic Route of 3972-56-3,Some common heterocyclic compound, 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, molecular formula is C10H13Cl, 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.

To a sealable reaction tube equipped with a stirring bar was charged with PdCl2(CH3CN)2 (2.6 mg, 0.01 mmol), TIP-Cy*Phine (11.1 mg, 0.02 mmol), Cs2CO3 (652 mg, 2 mmol), 1-tert-butyl-4-chlorobenzene (169 mg, 1 mmol), phenylacetylene (123 mg, 1 mmol) and 2 mL of acetonitrile. The tube was then sealed with a Teflon-lined septum and heated to 90¡ã C. for 6 h with vigorous stirring. The resulting suspension was cooled to room temperature, diluted with EtOAc and filtered through a pad of Celite. The filtrate was concentrated in vacuo affording the crude product which was purified by flash chromatography on silica gel using hexanes as the eluent to give a pure white solid (213 mg, 91percent). 1H NMR (600 MHz, CDCl3) delta=7.54 (d, J=5.8 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H), 7.37 (dd, J=21.8, 7.6 Hz, 5H), 1.35 (s, 9H). 13C NMR (151 MHz, CDCl3) delta=152.08, 132.13, 131.88, 128.86, 128.61, 125.90, 124.07, 120.79, 90.09, 89.28, 35.35, 31.75.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butyl-4-chlorobenzene, its application will become more common.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
Chloride – Wikipedia,
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Application of 118-69-4,Some common heterocyclic compound, 118-69-4, name is 2,6-Dichlorotoluene, molecular formula is C7H6Cl2, 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.

Ammoxidation runs were carried out in a fixed bed tubular quartz reactor, which is filled with 5g of catalyst particles prepared by the methods described in examples 1 to 3 and mixed with corundum particles of the same size in 1: 1 by weight ratio. A preheating zone is provided on the top of the catalyst bed. The catalyst was activated in a mixture of air and [NH3] at [400C] for 4 hours and then the catalytic runs were performed. The 2,6-DCT and [H20] were pumped in the mole ratio of 1: 15 to 20. The product stream was collected for every half-an-hour and analysed by gas chromatography. The reaction was carried out under the following reaction conditions. A reaction temperature of 350 to [400C] was used, and the GHSV comprised between 650-750 [H-‘.] The contact time consisted of 4.8 to 5.5 seconds. The mole ratio of 2,6-DCT : H20 : NH3: air was 1: 15: 3-4: 21, the molar concentration of 2,6-DCT was 2.4 % and the ratio of O/NH3 was 1. [1 %.]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichlorotoluene, its application will become more common.

Reference:
Patent; TESSENDERLO CHEMIE S.A.; WO2003/101939; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of Compound 4.1. Into a 50-mL round-bottom flask, was placed 2,4- dichloropyrrolo[2, l- J[l,2,4]triazine (200 mg, 1.06 mmol, 1.00 equiv), sodium carbonate (227 mg, 2.14 mmol, 2.00 equiv), (r,4r)-Nl, ^-dimethyl cyclohexane-l,4-diamine (276 mg, 1.94 mmol, 1.20 equiv) in ACN (20 mL). The reaction was stirred overnight at 80 C in an oil bath. Then it was concentrated in vacuo and the residue was purified by silica gel column chromatography with dichloromethane/methanol (20: 1). This resulted in 180 mg (58%) of 4.1 as a white solid.

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-Dichloropyrrolo[2,1-f][1,2,4]triazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; (102 pag.)WO2017/4134; (2017); A1;,
Chloride – Wikipedia,
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Related Products of 452-83-5, The chemical industry reduces the impact on the environment during synthesis 452-83-5, name is 2-Chloro-5-fluoroaniline, I believe this compound will play a more active role in future production and life.

Nitrosonium tetrafluoroborate (802 mg, 6.87 mmol) was added to a solution of 2-chloro-5-fluoroaniline (1.00 g, 6.87 mmol) in acetonitrile (50 mL) at 0 C. The resulting mixture was stirred for 1 h, then diluted with ethyl ether (150 mL). The precipitate was filtered and air-dried to give 2-chloro-5-fluorobenzenediazonium tetrafluoroborate (1-1) as an off-white solid. 1H NMR (300 MHz, CD3OD) delta 8.66 (ddd, 1H, J=6.7, 2.1, 1.0 Hz), 8.16 (m1, 2H).

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-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fraley, Mark E.; Garbaccio, Robert M.; Hartman, George D.; Hoffman, William F.; US2006/135594; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Sodium 4-chlorobenzenesulfinate

Example 74: 4-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]pyridine sodium 4-chlorobenzenesulfinate (207 mg, 1.04 mmol), 3-chloromethylpyridine hydrochloride (171 mg, 1.04 mmol) and potassium acetate (204 mg, 2.08 mmol) were added to n-butanol (5 ml).. The resulting mixture was stirred at 70C for 5 hours.. After cooling to room temperature, the solvent was concentrated under reduced pressure.. To the residue was added ethyl acetate and from the resulting mixture, the insoluble matter was filtered off.. The filtrate was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column and the from the fraction eluted with hexane:ethyl acetate (=2:3), a white solid (117 mg) was obtained. Then, a toluene (10 ml) solution of the resulting solid (52 mg), the 4-(methylsulfonyl)-1-butanol (90 mg, 0.592 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (140 mg, 0.582 mmol) was heated under reflux for 2 days under an argon atmosphere..

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 83121-15-7,Some common heterocyclic compound, 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline, molecular formula is C6H3Cl2F2N, 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 1: Preparation of 1-bromo-3,5-dichloro-2,4-difluorobenzene To a solution of 3,5-dichloro-2,4-difluorobenzenamine (9.9 g, 50.0 mmol) in HBr (200 mL) was added a solution of NaNO2 (3.45 g, 50.0 mmol) in H2O (80 mL) slowly under salt ice-bath, then the mixture was stirred for 2 h, and CuBr (7.15 g, 50.0 mmol) was added at 0 C. The mixture was stirred for additional 2 h, and then poured into water (100 mL), extracted with DCM, dried over NaSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography over silica gel eluted with PE to give compound 1-bromo-3,5-dichloro-2,4-difluorobenzene (6.2 g, yield 48%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 7.49 (t, J=7.2 Hz, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloro-2,4-difluoroaniline, its application will become more common.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example; 4-tert-Butyl-N-(4-chloro-5-fluoro-2-iodo-phenyl)-benzenesulfonamide; Step 1:; Iodine (873 mg, 3.44 mmol) was added to a solution of 4-chloro-3-fluoroaniline (500 mg, 3.44 mmol) and potassium hydroxide (193 mg, 3.44 mmol) in N,N-dimethylformamide (?DMF?) (10 mL) and the reaction was stirred at 60 C. for 18 hours. The crude mixture was subsequently partitioned with ethyl acetate (20 mL) and saturated ammonium chloride (20 mL) and the layers separated. The organic layer was washed with saturated ammonium chloride (3¡Á20 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (0-50% ethyl acetate in hexanes) to afford the desired iodoaniline (234 mg, 25%).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; US2009/5410; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H5ClF3N

Reference Example 13 7-Benzyloxy-N-[2-chloro-4-(trifluoromethyl)phenyl]-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine A mixture of 7-(Benzyloxy)-5-chloro-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine(53.0 g), 2-chloro-4-(trifluoromethyl)aniline(38.1 g), tris(dibenzylideneacetone)dipalladium(0)(5.10 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene(9.66 g)(a compound obtained in Reference Example 12), cesium carbonate(90.7 g) and 1,4-dioxane(1.05 L) was heated under reflux for 16 hours under argon atmosphere. After being cooled to room temperature, ethyl acetate(1 L) was added to the reaction mixture and filtered through Celite. The residue on the Celite was washed with ethyl acetate(1 L) and chloroform(500 mL), the washings were combined with the filtrate, and concentrated under reduced pressure. The resulting residue was crystallized and triturated in ethyl acetate-diethyl ether(1:1) and the crystalline was filtered and washed with ethyl acetate-diethyl ether(1:1). The obtained crystalline was dried to give the titled compound(43.7 g, 58percent yield) as a pale yellow crystalline. mp.189-192¡ãC, MS(APCI)M/z:540/S42[M+H]+.

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; Mitsubishi Tanabe Pharma Corporation; EP1903045; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 4584-46-7 as follows. HPLC of Formula: C4H11Cl2N

Provided in is step-by-step synthesis of PCA 1 and PCA 2. To make intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde, vanillin (1.52 g, 10 mmol), 2-chloro-dimethylethylamine HCI (2.16 g, 15 mmol), potassium iodide (332 mg, 2 mmol) and potassium carbonate (4.14 g, 30 mmol) were suspended in acetone and heated at reflux for 16 h. Next, volatiles were removed in vacuo and the resulting residue is redissolved in water and ethyl acetate. The organic layer was separated and washed with brine and dried with magnesium sulfate. Concentrating in vacuo resulted in 1.75 g (78%) of a yellow oil. NMR and mass spectrometry analysis of intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde is provided in to 4C: 1H NMR (400 MHz, Chloroform-d) delta9.82 (s, 1H), 7.41 (dd, J=8.2, 1.9 Hz, 1H), 7.37 (d, J=1.9 Hz, 1H), 6.96 (d, J=8.2 Hz, 1H), 4.17 (t, J=6.1 Hz, 2H), 3.89 (s, 3H), 2.79 (t, J=6.1 Hz, 2H), 2.32 (s, 6H). () 13C NMR (101 MHz, CDCl3) delta191.2, 154.0, 150.0, 130.3, 127.0, 111.7, 109.3, 67.4, 58.0, 56.2, 46.3. () ESI-MS [M+H]: Calculated: 224.1; Observed: 224.1 ()

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Board of Trustees of the Leland Stanford Junior University; Velema, Willem Arend; Kool, Eric T.; (79 pag.)US2019/264205; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

To a suspension of Intermediate 5 (100 g, 0.396 mol) in acetonitrile (4 L) was added 2-fluoro-3-chloroaniline (60.5 g, 0.416 mol) and the reaction mixture was heated to 80 C. overnight. The precipitate was collected by filtration and dried in vacuo to afford Intermediate 6 (181 g, 80% purity) as white solid which was used for next step directly without purification. 1H NMR (DMSO-d6 400 MHz): delta 8.93 (s, 1H), 8.82 (s, 1H), 7.67-7.63 (m, 1H), 7.59 (s, 1H), 7.56-7.52 (m, 1H), 7.39-7.35 (m, 1H), 4.02 (s, 3H), 2.39 (s, 3H).

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; ASTRAZENECA AB; LI, David Yunzhi; WANG, Jiabing; YANG, Zhenfan; ZENG, Qingbei; ZHANG, Xiaolin; US2014/255428; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics