Month: November 2020

A common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. 104-52-9.

To a suspended solution of AlCl3 (8.69 g, 65.2 mmol) and 3-chloropropionylchloride(9.97 g, 64.5 mmol) in dichloromethane (70 mL) was added 3-phenylpropylchloride(7.91 g, 62.8 mmol). The mixture was stirred at room temperature for 4 h and thenquenched by saturated NaHCO3 aq (100 mL). The mixture was extracted with diethylether (100 x 3 mL). The collected organic layer was washed with water (100 x 2 mL)and saturated NaCl aq (100 mL) and then dried (MgSO4). The solvent was evaporatedand the residue was washed with hexane to give the product as white solid (9.73 g,63%).

The synthetic route of 3-Phenylpropyl Chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishimoto, Yoshihiro; Yazawa, Satoshi; Kiyokawa, Kensuke; Kajiki, Takahito; Tsukahara, Yasunori; Yamauchi, Tomohisa; Wada, Yuji; Baba, Akio; Yasuda, Makoto; Chemistry Letters; vol. 46; 8; (2017); p. 1116 – 1118;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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 202197-26-0. 202197-26-0

Example 17 O-{4-[-3-chloro-4-(3-fluorobenzyloxy)-phenylamino]-quinazolin-6-yl}-acetate 6-acetoxy-4-chloroquinazoline (0.90 g, 4.04 mmol) and 3-chloro-4-(m-fluoro-benzyloxy)-aniline (1.00 g, 3.97 mmol) were dissolved into 40 mL of isopropanol, and the mixture was stirred under reflux for 3 h. A lot of light grey solid was deposited, which was filtered, and the filter cake was washed with small quantity of ethyl acetate and dried under vacuum at 60 C. overnight to obtain the title compound (1.65 g, 95%). 1H-NMR (400 MHz, CDCl3): delta8.68(1H, s), 7.89-7.81 (2H, m), 7.58-7.48 (2H, m), 7.40-7.32 (1H, m), 7.27-7.19 (3H, m), 7.16 (1H, d, J=2.46 Hz), 7.07-6.96 (2H, m), 5.14 (2H, s), 2.11 (3H, s).

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 3-Chloro-4-((3-fluorobenzyl)oxy)aniline.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICALS, INC.; US2008/300248; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

This experiment was carried out in two batches of the same scale. n-Butyllithium (2.5 M solution in hexanes; 32.8 mL, 82.0 mmol) was slowly added to a -70 C. solution of 1-bromo-4-chloro-2-fluorobenzene (17.2 g, 82.1 mmol) in diethyl ether (100 mL), while the temperature of the reaction mixture was maintained below -60 C. After the reaction mixture had been stirred at -70 C. for 20 minutes, a solution of 3-bromo-2-hydroxybenzaldehyde (5.5 g, 27 mmol) in diethyl ether (100 mL) was slowly added, while the reaction temperature was maintained below -60 C. After a further 1 hour of stirring at -70 C., the reaction was quenched by addition of aqueous ammonium chloride solution (50 mL) at -70 C., and the resulting mixture was diluted with water (100 mL). The two batches were combined at this point and extracted with ethyl acetate (400 mL); the organic layer was washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 7% ethyl acetate in petroleum ether) afforded C1 as a white solid. Combined yield: 15.7 g, 47.4 mmol, 88%. 1H NMR (400 MHz, chloroform-d) delta 7.44 (dd, J=8.0, 1.5 Hz, 1H), 7.37 (dd, J=8.1, 8.1 Hz, 1H), 7.15 (br dd, J=8.5, 2.1 Hz, 1H), 7.12-7.05 (m, 2H), 6.80 (dd, J=7.8, 7.8 Hz, 1H), 6.78 (s, 1H), 6.31 (d, J=4.8 Hz, 1H), 3.02 (brd, J=4.9 Hz, 1H).

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Edmonds, David James; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Lian, Yajing; Limberakis, Chris; Londregan, Allyn T.; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (127 pag.)US2019/382384; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-70-3, name is 1,3,5-Trichlorobenzene, belongs to chlorides-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. 108-70-3

To a 250 ml single-necked flask was placed 9.5 g (52.4 mmol) of 1,3,5-trichlorobenzene and 100 ml of ultra-dry tetrahydrofuran under argon protection and minus 78 degrees Celsius. Then, 26.3 ml (2 Torr, 52.6 mmol) of lithium diisopropylamide in tetrahydrofuran/n-hexane solution was added dropwise, and the mixture was stirred at minus 78 C for 30 minutes. Then, 10.0 g (47.7 mmol) of Compound A1 was added, and stirring was continued for 2 hours at minus 78 C. The reaction was then slowly warmed to room temperature and quenched by the addition of 200 mL of saturated aqueous ammonium chloride. The combined organic layers were washed with brine (25 mL) After evaporating the solvent, it was purified by column chromatography using methylene chloride: petroleum ether: 1:1 (volume ratio) as eluent to afford 17.5 g of product A2, yield 94%.

Statistics shows that 108-70-3 is playing an increasingly important role. we look forward to future research findings about 1,3,5-Trichlorobenzene.

Reference:
Patent; Jilin University; Li Feng; Ai Xin; Zhang Ming; (25 pag.)CN108191739; (2018); A;,
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. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 108-41-8

Example 6: 3-Chlorobenzoic Acid In a 100 ml jacketed vessel, 200 ml of acetic acid, 0.08 g of cerium(III) acetate, 4.9 g of sulfuric acid and 12.65 g of 3-chlorotoluene were initially charged. The mixture was cooled to 16 C. and 5.15 g of ozone were introduced within a period of 75 minutes. After completion of ozonolysis, the ozone present in the solvent was blown out using nitrogen. Analysis of the reaction mixture by means of HPLC or GC gave the following results: 3-chlorotoluene: >0.1%; 3-chlorobenzoic acid: 98%

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jary, Walther; Poechlauer, Peter; Ganglberger, Thorsten; US2003/216577; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

3386-33-2, Adding a certain compound to certain chemical reactions, such as: 3386-33-2, name is 1-Chlorooctadecane, belongs to chlorides-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 3386-33-2.

Diallylphenol (3.48 gm, 0.02 mol) was diluted in dimethyl sulfoxide (50 ml) and sodium hydroxide (0.8 gm, 0.02 mol) added to the solution followed by 1-chlorooctadecane (5.78 gm, 0.02 mol) and heated at 80 C. for 2 hrs. After cooling and diluting with water, the reaction mixture was extracted with hexane, dried over MgSO4 filtered and evaporated to give the desired product. MS m/z 426. (M+ calcd for C30H50O=426). H NMR (300 MHz, CDCl3) d 0.80 (t ,3, CH3), 1.25 (s, 32, CH2).1.75-1.80 (m, 2, CH2), 3.30-3.40 (d, 4, CH2), 3.70-3.80 (t, 2, OCH2), 5.05-5.21(m, 2, CH2 vinyl), 5.95-6.10 (m, 2,CH2 vinyl), 7.00-7.20(m, 3, aromatic). Oxidation with MCPBA as described in Example 1 gave 2,6-di(epoxypropyl)phenyl octadecyl ether. MS m/z 458 (M+ calcd for C30H50O3=458). H NMR (300 MHz, CDCl3) d 0.80 (t, 3, CH3), 1.25 (s, 30, CH2), 2.60-2.70 (m, 2, CH2 epoxypropyl), 2.75-3.10 (m, 6, CH2 epoxypropyl), 3.20-3.30 (m, 2, epoxypropyl CH), 3.55-3.75 (t, 2, CH2), 7.10-7.25 (m, 1, aromatic), 7.40-7.60 (m, 2, aromatic).

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, 1-Chlorooctadecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pews, R. Garth; US2005/90673; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, A common compound: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Reference Example 1 To 100 ml of acetic acid solution containing 20 g of 2-benzylamino-4-chloroaniline was added 15 ml of O-methyl-trichloroacetoimidate at 0 to 25 C., and stirred the mixture at room temperature for 3 hours. Then water was added to the reaction mixture, the separated crystals were collected by filtration to obtain 29.6 g of 1-benzyl-6-chloro-2-trichloromethylbenzimidazole in the form of pale brown powder. 1 H-NMR (250 MHz, DMSO-d6) delta ppm: 5.94 (2H, s), 7.04 (2H, d, J=6.5 Hz), 7.25-7.5 (5H, m), 7.88 (1H, d, J=9.0 Hz).

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US5998437; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4 name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

Intermediate Q6-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine A mixture of 4.18 g (18 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 2.95 g (18.9 mmol) of 3-chlorophenylbronic acid, 0.83 g (0.72 mmol) of tetrakis(triphenylphosphine)palladium (0) and 32.3 ml of 2 M aqueous sodium carbonate solution are heated to boiling under in 188 ml of 1,4-dioxane for 12 h.The reaction mixture obtained in this way is mixed with sat. aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with sat. aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off. In the final purification by chromatography on silica gel, 3.46 g (73%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.43 (d, 1H); 7.44 (dd, 1H); 7.53 (t, 1H); 8.05 (dt, 1H); 8.16 (t, 1H); 8.29 (d, 1H); 8.38 (s, 1H) ppm.MS (ESI+): m/z=264 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; PRIEN, Olaf; Eis, Knut; Bader, Benjamin; Guenther, Judith; Von Bonin, Arne; US2009/93475; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, belongs to chlorides-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 1871-57-4, 1871-57-4

General procedure: To a cooled solution (5 C) of the corresponding 4,6-O-(R)-benzylidene-d-hexopyranoside derivative (obtained using the procedure describe by our group2c) (35.4 mmol) in dry THF (70 mL) were added, successively, freshly powdered potassium hydroxide (7.0 g, 125 mmol), 18-crown-6 (0.38 g, 1.4 mmol), and 3-chloro-2-chloromethylpropene (4.1 mL, 35.4 mmol). The reaction mixture was stirred at this temperature for 3 h, and left at room temperature until all the starting material had been consumed, as monitored by TLC (5-7 days, approximately), then diluted with dichloromethane (60 mL) and washed successively with water and aqueous saturated solution of sodium bicarbonate, dried (MgSO4), filtered, and the filtrate was evaporated to dryness.

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, 3-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vega-Perez, Jose M.; Vega-Holm, Margarita; Perinan, Ignacio; Palo-Nieto, Carlos; Iglesias-Guerra, Fernando; Tetrahedron; vol. 67; 2; (2011); p. 364 – 372;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, Adding some certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 ¡Á 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

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 2533-69-9.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics