Month: September 2021

56961-77-4, These common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, 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.

1-bromo-2,3-dichlorobenzene (15.0 g, 66.4 mmol) and aniline (12.7 g, 136.1 mmol) were added to toluene in a three-necked flask. Dissolved in 450ml sodium tert-butoxide (9.6g, 99.6mmol), bis (tri-tert-butylphosphine) palladium (0) (0.7 g, 1.3 mmol) was added thereto, followed by stirring for 6 hours under reflux conditions under argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, H 2 O was added thereto, and the reaction solution was transferred to a separatory funnel to extract. The extract was dried over MgSO 4, concentrated and the sample was purified by silica gel column chromatography to give 14.7 g of intermediate A-1. (Yield 75%)

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 56961-77-4.

Reference:
Patent; LG Chem, Ltd.; Seo Sang-deok; Park Tae-yun; Lee Dong-hun; (32 pag.)KR2019/141620; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, 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. Formula: C7H7ClO2S

Preparation 7: N-(2-bromoethyl)(phenyl)methanesulfonamide K2C03 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2S04, filetered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200 – 300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound /V-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. H NMR (300 MHz, CDC13) delta 7.40 (m, 5H), 4.58 (m, IH), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

The synthetic route of Phenylmethanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1716-42-3, These common heterocyclic compound, 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, 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.

EXAMPLE 40 A mixture of 6.5 parts of 1-[(4-fluorophenyl)methyl]-2-(4-piperidinylmethyl)-1H-benzimidazole, 4.2 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 30 minutes using a water separator. 5.2 Parts of 1-(3-chloropropoxy)-4-fluorobenzene were added at reflux temperature and stirring was continued for 3 hours at this temperature using a water separator. After cooling to room temperature, the salts were filtered off and the filtrate was washed twice with water, dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanone. The salt was filtered off, washed with 2-propanone and crystallized from methanol. The product was filtered off and dried in vacuo at 80° C., yielding 7 parts (53percent) of 2-[[1-[3-(4-fluorophenoxy)propyl]-4-piperidinyl]methyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole ethanedioate (1:2); mp. 186.7° C. (119).

Statistics shows that 1-(3-Chloropropoxy)-4-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1716-42-3.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4695575; (1987); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-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.

To a solution of diisopropylamine (76 mL, 0.4 mol) in anhydrous THF (664 niL) and n-hexane (220 mL) was added 2.5 M «-BuLi (160 mL, 0.4 mol) dropwise* at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1 – bromo-3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at -78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to room temperature during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l -bromo-3- fluoro-2-iodobenzene (1 15 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2007/117560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 6775-78-6, 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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Chloroimidazo[1,2-b]pyridazine (8.5 g, 0.055 mol) and N-bromosuccinimide (10.0 g, 0.056 mol) were combined in chloroform (250 mL) and refluxed for 4 hours. The reaction was cooled with an ice bath and the solids filtered. The filtrate was diluted with chloroform (150 mL) and saturated Na2CO3 solution (100 mL) and then vigorously stirred for an hour. The organic phase was washed with more saturated Na2CO3 solution and dried over MgSO4. After evaporation, 3-bromo-6-chloro-imidazo[1,2-b]pyridazine was obtained as a tan solid (12.64 g, 98%).MS (ESI (+)m/z): 233.87 (M+H+)1H NMR (CDCl3-d1, 300 MHz), delta 7.83 (d, J=9.3 Hz, 1H), 7.72 (s, 1H), 7.05 (d, J=9.3 Hz, 1H).

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, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Biogen Idec Ma Inc.; US2011/21513; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 697-88-1,Some common heterocyclic compound, 697-88-1, name is 4-Bromo-2,6-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

Pd (OAc) 2 (186 mg), P (o-Tol) 3 (505 mg), Et3N (1.73 ml), 4-bromo-2,6- dichlorobenzeneamine (2.0 g) and acrylamide (885 mg) were dissolved in MECN (15 ml) and N2 was bubbled through the reaction mixture for at least 20 minutes. Then a cooler was mounted strictly under nitrogen atmosphere. The reaction mixture was heated at 70 C overnight. The reaction mixture was allowed to cool to 20 C and was diluted with CH2CI2 and washed with saturated aqueous NAHC03 (2x) and dried with brine and NA2SO4. The residue was sonicated in diisopropyl ether and filtered off. Yield: 0.55 g of intermediate 18 (30%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,6-dichloroaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 344-19-4, 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. 344-19-4, name is 2,6-Dichloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cu-powder (5.3 g) was added with stirring to 2,6-dichloro-4-fluoro-aniline (100 g, 0.56 mol) dissolved in diethyldisulfide (400 mL) and the mixture was heated at 80 C. Tert-butyl nitrite (86g, 1 .5 equiv.) was added slowly over a period of 1 hour (exothermic reaction) and stirring was continued for an additional hour at 80 C.Work-up: Excess diethyl disulfide was evaporated in vacuo and the residual crude was treated with diluted aqueous hydrochloric acid. The aqueous phase was extracted with toluene. Thr organic phase was washed sequentially with hydrochloric acid and water, dried over mag35 nesium sulfate. Evaporation of the solvent gave 1 ,3-dichloro-2-ethylsulfanyl-5-fluoro-benzene asa brownish oil (111 g, 0.50 mol, 89%) which was used without further purification in the next step.1H NMR (CDCI3, 400 MHz): D = 7.2 (d, 2 H), 2.9 (q, 2 H), 1.2 (t, 3H).

The synthetic route of 2,6-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KRAUS, Helmut; CALO, Frederick; WITSCHEL, Matthias; SEITZ, Thomas; NEWTON, Trevor William; MASSA, Dario; MIETZNER, Thomas; PASTERNAK, Maciej; KREUZ, Klaus; EVANS, Richard Roger; LERCHL, Jens; WO2014/184016; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 202865-57-4, name is 1-Bromo-2,5-dichloro-3-fluorobenzene, 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 202865-57-4, COA of Formula: C6H2BrCl2F

6-chloro-2-fluoro-3-methylphenol (3.3 g, 20.55 mmol) and 18-crown-6 (1.086 g, 4.11 mmol) were dissolved in dry DMSO (50 ml.) and treated with 20% potassium t- butoxide in THF (1 1.50 g, 20.55 mmol) for 15 minutes at room temperature. 1- bromo-2,5-dichloro-3-fluorobenzene (7.21 g, 29.6 mmol) was added in one portion and the reaction mixture heated at 1 100C for 3 days at which time LC-MS indicated nearly complete consumption of phenol and formation of a major new product. Addition of water to the reaction mixture resulted in a brown gummy oil which was extracted with EtOAc. The organic phase was isolated, washed with brine four times, dried over MgSOphi filtered and concentrated to dryness to give a brown syrup. This material was filtered through a plug of 45 g silica gel which was eluted with 500 ml_ DCM. The filtrate was concentrated to an amber oil and crystallized from EtOH and a few drops of water. This mixture was cooled in an ice bath, filtered, and the precipitate washed with three portions of cold EtOH to give 2-[(3-bromo-2,5- dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (4.0 g, 10.40 mmol, 50.6 % yield) as a cream solid. 1 H NMR (400 MHz, DMSO-c/6) delta ppm 7.73 (s, 1 H), 7.29 – 7.47 (m, 2 H), 6.81 (s, 1 H), 2.29 (s, 3 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; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 626-43-7, 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. 626-43-7, name is 3,5-Dichloroaniline, This compound has unique chemical properties. The synthetic route is as follows.

5.2.1 5,7-Dichloro-2-methylquinoline (B-TDMQ5) To a solution of 3,5-dichloroaniline (3.24 g, 20 mmol) in HCl (12 M, 15 mL) at 0 C acetaldehyde was added dropwise, under stirring. The reaction medium was kept at 0 C for 15 min and the temperature was gradually increased to 80 C. The mixture was stirred at 80 C for 4 h. The resulting mixture was poured into ice-cold water and neutralized with aqueous ammonium. After extraction with CH2Cl2, the organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude mixture was purified by silica gel flash column chromatography (ethyl acetate/petroleum ether, 1/20, v/v). After evaporation of the eluent, B-TDMQ5 was obtained as a yellow solid (2.88 g, 68%). 1H NMR (400 MHz, CDCl3): delta = 8.40 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 2.0 Hz, 1H), 7.55 (d, J =2.0 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H), 2.76 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 3,5-Dichloroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Weixin; Huang, Meijie; Bijani, Christian; Liu, Yan; Robert, Anne; Meunier, Bernard; Comptes Rendus Chimie; vol. 21; 5; (2018); p. 475 – 483;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 an oven-dried screw-capped reaction tube equipped with a magnetic stirring bar theketone (1 eq), amine (2.8 eq), 4-nitrophenyl azide (2 eq), acetic acid (10 molpercent) and 4 Amolecular sieves (50 mg) were added. The reaction mixture was dissolved in toluene(0.3M) and stirred at 100 °C for 18 hours. The crude reaction mixture was then directlypurified by column chromatography (silica gel) at first with dichloromethane (DCM) aseluent to remove all 4-nitroaniline formed during the reaction followed by using a mixtureof heptane and ethyl acetate as eluent to afford the corresponding 1,2,3-triazoles asyellow oil.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karypidou, Konstantina; Ribone, Sergio R.; Quevedo, Mario A.; Persoons, Leentje; Pannecouque, Christophe; Helsen, Christine; Claessens, Frank; Dehaen, Wim; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3472 – 3476;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics