Tag: M.W=200-300

27139-97-5, 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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below.

Step 1 Ethyl (E)-3-(5-chloro-2-methylphenyl)-2-propenoate To 2-bromo-4-chloro toluene (20.0 g; 97.3 mmol) in 300 mL of THF at -78¡ã C. was added n-BuLi 2.5M (40.8 mL) dropwise. After 20 min. 1-formylpiperidine (11.4 mL; 103.0 mmol) in 10 mL of THF was added dropwise. After 30 min the reaction mixture was brought to 0¡ã C. and quenched with HCl (10percent) and diluted with EtOAc. The organic phase was collected, dry and the solvent evaporated to yield 13.3 g (89percent) of 5-chloro-2-methylbenzaldehyde.

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; Merck Frosst Canada & Co.; US6242493; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, molecular formula is C7H6BrClO, 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. 50638-46-5

Step 1; Scheme 30:; To a mixture of 4-bromo-3-chloro anisole (35 g, 0.159 mol), KCl (11.9 g, 0.160 mol, 1 eq.), K2CO3 (33 g, 0.238 mol, 1.5 eq) in 400 mL DMF in a sealed tube was added acrolein diethylacetal (73 mL, 0.479 mol, 3 eq.) and Bu4NOAc (96 g, 0.318 mol, 2 eq.). N2 was bubbled through the mixture and Pd(OAc)2 (1.1 g, 4. mmol, 3 mol %) was added. The reaction mixture was heated in an oil bath for 6 hr at 100 C. then cooled in an ice-bath. 300 mL of water was then added, followed by 500 mL of 1N HCl. The ice-bath was removed and the mixture was stirred for 30 min. The solution was extracted with ethyl acetate once then with diethyl ether 3 times. The combined organic layer washed with water, brine, dried over MgSO4, filtered and concentrated to provide the crude product which was recrystallized from hot ethyl acetate-hexanes to provide 15.5 g of crystalline 3-(2-chloro-4-methoxy-phenyl)-propenal. The mother liquor was concentrated and chromatographed with 10% ethyl acetate to provide another 5.6 g of 3-(2-chloro-4-methoxy-phenyl)-propenal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50638-46-5, its application will become more common.

Reference:
Patent; Chackalamannil, Samuel; Chelliah, Mariappan V.; Clasby, Martin C.; Eagen, Keith A.; Scott, Jack D.; Wang, Yuguang; Xia, Yan; Greenlee, William J.; US2007/197628; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life. 13918-92-8

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 13918-92-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 328-84-7, name is 3,4-Dichlorobenzotrifluoride, molecular formula is C7H3Cl2F3, 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. 328-84-7.

Example- 1; N-methylpyrrolidone (1050 ml) was charged in an autoclave along with 102 g anhydrous activated potassium fluoride, 377 g 3,4- dichlorobenzotrifluoride was added. Ammonia (158 g) gas was passed in the reactor from the pressure pot at ambient temperature. The content of the reactor was heated to 245-250¡ãC over a period of 2 hours to get reactor pressure of 30-32 kg/cm2. Excess NH3 was fed from the pressure pot to maintain the reactor pressure at 38-40 kg/cm at 245-250¡ãC liquid temperature. Reaction mixture was maintained at 245-250¡ãC and at 38-40 kg/cm2 pressure for further 8 hours. Reaction mixture was cooled to ambient temperature and NH3 was vented and recovered. Reaction mixture was filtered and on fractionation gave 77percent yield of 2-chloro-4- trifluoromethylaniline and 13percent yield of 2-chloro-5-trifluoro methyl aniline based on consumed 3,4-dichlorobenzotrifluoride.

The synthetic route of 3,4-Dichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GHARDA, Keki Hormusji; WO2011/107998; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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. 1127-85-1

EXAMPLE XIV STR44 A mixture of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline ?prepared according to the procedure described by M. Botta et al., 40, Tetrahedron, (1984), 3313! (500 mg, 2.4 mmol), phenylhydrazine (270 mg, 2.5 mmol) and N,N-diisopropylethylamine (1 ml, 5.7 mmol) in THF (50 ml) was heated at reflux temperature overnight. The reaction was cooled to room temperature and phosgene (200 ml, 20% in toluene) was added slowly and stirred for an additional 10 min. The mixture was poured into water and extracted with ethyl acetate (3*50 ml). The combined organic layers were washed with brine, dried over Na2 SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one, m.p. 205-207 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1127-85-1, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5677309; (1997); A;,
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 41965-95-1 as follows. 41965-95-1

Methyl 2-chloro-4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate, 14 To a heterogenous mixture of quinoline 13 (3.56 mmol) and 3-chloro-4-methoxy benzylamine.HCl (3.92 mmol) in NMP (15 mL) was added iPr2NEt (8.90 mmol). The reaction mixture was heated to 80 C. for 3 h. Subsequently, cooled the reaction mixture to ambient temperature and added 1M aqueous HCl and EtOAc. The resulting layers were separated and the organic layer washed with water (3*) followed by brine (1*). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in a minimum amount of hot EtOAc and allowed to cool to ambient temperature. Hexanes was then added to the solution and the intermediate 14 (80% yield) precipitated out and was collected by vacuum filtration. 1H NMR (300 MHz, CDCl3) delta8.20 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 7.82 (d, 1H, J=7.5 Hz), 7.38 (s, 1H), 7.27-7.22 (m, 1H), 6.98 (d, 1H, J=8.4 Hz), 6.26 (s, 1H), 4.54 (d, 2H, J=4.8 Hz), 3.95 (s, 3H), 3.93 (s, 3H).

According to the analysis of related databases, 41965-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
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. 101-79-1, name is 4-(4-Chlorophenoxy)aniline, A new synthetic method of this compound is introduced below., 101-79-1

A solution of 4-tert-butyl-2-aminopyridine (0.177 g, 1.18 mmol, 1 equiv.) in 1.2 mL of anh. CH2Cl2 (1.2 mL) was added to CDI (0.200 g, 1.24 mmol, 1.05 equiv) and the mixture was allowed allowed to stir under argon at room temperature 1 d. To the resulting solution was added 4-(4-chlorophenoxy)aniline (0.259 g, 1.18 mmol, 1 equiv.) in one portion. The resulting mixture was stirred at room temperature for 1 d, then was treated with a 10percent citric acid solution (2 mL) and allowed to stir for 1 h. The resulting organic layer was extracted with EtOAc (3*5 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The resultant residue was treated with CH2Cl2 (10 mL) and a 1N aqueous NaOH solution. This mixture was allowed to stir overnight. The resulting organic layer was extracted with CH2Cl2 (3*5 mL). The combined organic layers were (MgSO4) and concentrated in vacuo. The resultant solids were suspended in diethyl ether (10 mL) and sonicated for 15 minutes. The resulting white solid were dried to give N-(4-tert-butylpyridyl)-N’-(4-(4-chlorophenoxy)phenyl) urea (42 mg, 9percent): mp 198-199¡ã C.

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 CORPORATION; US2002/165394; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

874-17-9, Adding some certain compound to certain chemical reactions, such as: 874-17-9, name is 4-Chloro-2,6-dibromoaniline, 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 874-17-9.

Under a nitrogen stream, 2,6-dibromo-4-chloroaniline (20.0 g, 70.08 mmol),Pd (PPh3) 4 (4.04 g, 3.50 mmol) was added to the reaction solution after stirring the mixture with phenylboronic acid (8.54 g, 83.01 mmol), K2CO3 (29.05 g, 210.24 mmol) and Toluene / H2O / EtOH Mmol) were added thereto, and the mixture was stirred at 100 C for 5 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and subjected to column chromatography to obtain the objective compound 4-chloro-2,6-diphenylaniline (15.8 g).

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 874-17-9.

Reference:
Patent; Doosan Corporation; Son, Hyo Suk; Sim, Jae Uii; Lee, Jae Hun; Park, Ho Chul; Lee, Chang Jun; Sin, Jin Yong; Baek, Young Mi; (46 pag.)KR2015/87045; (2015); A;,
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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., 1996-30-1

A mixture of 2-30 (1.04 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified by column chromatography on silica gel eluting with PE/ethyl acetate from 20/1 to 10/1 to provide intermediate 2-31 (806 mg, 63% yield) as a yellow solid. LCMS (m/z): 173 [M-H-82j -.

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; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

a) S-Bromo-e-il-methyl-piperidin^-yloxyJ-imidazotl^-i lpyridazine To a suspension of NaH (60% in oil, 0.17 g, 4.31 mmol) in dry THF (5 mL) at 0 C was added a solution of 4-hydroxy-/V-methyl piperidine (0.50 g, 4.31 mmol) in dry THF (5 mL). The reaction mixture was stirred a 0C for 5 min then at RT for 15 min. The reaction mixture was cooled back to 0C and a solution of 3-bromo-6-chloroimidazo[1 ,2- ?>]pyridazine (0.50 g, 2.15 mmol) in dry THF (10 mL) was added dropwise. The reaction mixture was then allowed to warm up slowly to RT and stirred for 4 h. The reaction mixture was quenched by addition of water (10 mL), diluted with EtOAc (100 mL) and washed with water (2 x 50 mL). The organic layer was dried and concentrated in vacuo. Purification by column chromatography (EtOAc-2M NH3 in MeOH 5-100%) gave a solid (0.35 g, 53%); 1H NMR (400 MHz, DMSO-d6) delta ppm 8.04 (d, J=9.6 Hz, 1 H), 7.73 (s, 1H), 6.93 (d, J=9.6 Hz, 1 H), 4.99 (m, 1 H), 2.75-2.56 (m, 2H), 2.27-2.13 (m, 5H), 2.13-2.01 (m, 2H), 1.90-1.65 (m, 2H); m/z (ES+APCI)+: 311/313 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics