Category: chlorides-buliding-blocks

6940-78-9, name is 1-Bromo-4-chlorobutane, 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. 6940-78-9

Example Al l; a. Preparation of intermediate 75; A solution of l-bromo-4-chlorobutane (22.25 ml, 0.19 mol) in diethyl ether (100 ml) was added dropwise (under N2 atmosphere) to a suspension of activated Mg turnings (4.67 g, 0.19 mol) in diethyl ether (100 ml). Some crystals of iodine were also added. The temperature in the flask increased, and the orange colour turned to white. Once the addition of l-bromo-4-chlorobutane was completed, the reaction was cooled in an ice- bath and 2-naphthalenecarboxaldehyde (20.00 g, 0.13 mol) was added dropwise as a solution in THF (200 ml, dry). The reaction mixture was stirred in the ice-bath for 4 hours. Then the mixture was quenched with NH4Cl 1 N. Both phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography (eluent: n- hexane/EtOAc 20:1). The desired fractions were collected and the solvent was evaporated, yielding intermediate 75.

Statistics shows that 6940-78-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-4-chlorobutane.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/68266; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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. 1996-29-8

In a 200 mL three-necked flask, the obtained white solid and 4.2 g (20 mmol) of 1-bromo-4-chloro-2-fluorobenzene, 6.1 g (19 mmol) of cesium carbonate were placed. To this mixture, 30 mL of N-methyl-2-pyrrolidone was added and the mixture was degassed by stirring while reducing the pressure. After degassing, the mixture was stirred at 120 C. for 7 hours under a nitrogen stream. After stirring, water was added to this mixture, and after ultrasonic irradiation, filtration was carried out to obtain a solid. The obtained solid was washed with water and ethanol. This solid was purified by silica gel column chromatography (developing solvent: toluene). The obtained solid was recrystallized from toluene / ethyl acetate to obtain 1.9 g of a white solid in a yield of 42%. The synthesis scheme of Step 2 is shown below.

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, 1996-29-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Ltd.; Takeda, Kyoko; Ozaka, Harue; Seo, Tetsushi; Suzuki Tsune Toku; Hashimoto Naoaki; Takida Yuu Kai; (218 pag.)JP6339749; (2018); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-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 21 6(3-Chloro-4-fluoro-phenyl)-4-isopropyl-3,4-dihydro-1H-quinoxalin-2-one A mixture of (3,4-dihydro-4-isopropyl-2-oxoquinoxalin-6-yl)boronic acid (2.4 g, 10 mmol), 4-bromo-2-chlorofluorobenzene (2 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml) and water (25 mol) was heated to reflux for 6 hrs. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3*). The combined organic layers were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude product (2.9 g, 91%). Recrystallization from EtOAc/hexane afforded the title compound, mp 208-213 C.: 1H-NMR (DMSO-d6) delta 1.16 (d, J=6.59 Hz, 6H), 3.56 (s, 2H), 4.22 (septet, J=6.59 Hz, 1H), 6.86 (d, J=7.91 Hz, 1H), 6.96 (dd, J=7.91, 1.76 Hz, 1H), 7.01 (d, J=1.76 Hz, 1H), 7.43 (t, J=9.01 Hz, 1H), 7.61 (m, 1H), 7.82 (dd, J=7.14, 2.31 Hz, 1H), 10.47 (s, 1H). MS (EI) m/z 318 [M]++ 1 chlorine.

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 60811-21-4.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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. 363-51-9.

To a solution of 6.05 g (19.0 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 3.88 g (26.6 mmol) of 2-chloro-6-fluoroaniline in 30.3 ml dichloromethane were added 23.2 ml (133 mmol) of DIPEA, and the mixture was stirred at RT for 4 h. Subsequently, 2.63 g (19.0 mmol) of potassium carbonate were added and the mixture was heated under reflux overnight. The mixture was diluted with 200 ml of DCM and washed twice with 75 ml of 1 M aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The suspension obtained was stirred with 40 ml of tert-butyl methyl ether, and the precipitate was filtered off with suction, washed with 10 ml of tert-butyl methyl ether and dried under high vacuum. 5.70 g (64% of theory, 81% purity) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.88 (s, 1H), 8.64 (d, 1H), 7.76-7.57 (m, 4H), 4.25 (q, 2H), 1.28 (t, 3H). LC-MS (Method 3): Rt=1.86 min; 381 [M+H]+.

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-6-fluoroaniline, its application will become more common.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6775-78-6, A common compound: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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.

A mixture of 6-chloro-imidazo[ l ,2-b]pyridazine (200 mg, 1 .30 mmol, 1.00 equiv), bis(triphenylphosphine)palladium(Il) dichlonde (200 mg, 0 28 mmol, 0.22 equiv), and tnethylamine (0.5 mL) in methanol (4 mL) was stirred under carbon monoxide ( 10 atm) in a 50-mL pressure reactor overnight at 1 10 C. The solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 /1 ) to give 1 00 mg (43%) of the title compound as a yellow solid. NMR (300 MHz, CDCL) 5 8.16 (s, l H), 8.08 (d, J = 9,6 Hz, 1 H), 7.94 (s, 1 H), 7.77 (d, J = 9.6 Hz, 1 H), 4.09 (s, 3H).

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; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); 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. 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. 344-19-4

A.9.1. Synthesis of 1 ,3-dichloro-5-fluoro-2-(prop-2-en-1 -yl)benzene a23. To a solution of allyl bromide (21 .6 mL, 249.9 mmol) in degassed ACN (80 mL) was added fert-butyl nitrite (3.99 mL, 33.22 mmol). A solution of 2,6-dichloro-4-fluoroaniline (3 g, 16.66 mmol) in ACN (5 mL) was added dropwise within 20 min. The reaction mixture was stirred at rt for 90 min. and concentrated under vacuum. The residue was taken up EtOAc and washed with water. The organic layer was dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by column chromatography using 1 % EtOAc in hexanes as eluent to afford 1 .4 g of 1 ,3-dichloro-5-fluoro-2-(prop-2-en-1 -yl)benzene a23. Yield: 41 % LCMS: 205 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta 7.54 (d, J = 8.4 Hz, 2H), 5.91 -5.82 (m, 1 H), 5.07 (d, J = 9.9 Hz, 1 H), 4.91 (m, 1 H), 3.59 (d, J = 5.2 Hz, 2H).

The synthetic route of 344-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; VALADE, Anne; JNOFF, Eric; ATES, Ali; BURSSENS, Pierre; SKOLC, David; (211 pag.)WO2016/55479; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, This compound has unique chemical properties. The synthetic route is as follows., 7781-10-4

A portion of the compound obtained in Step 1 above (1.36 mmol) and lithium hydroxide monohydrate (571 mg, 13.62 mmol, 10 eq.) were treated at 110 C. in PDO-water (40 ml, 1:1). The v/v) mixture is stirred for 7-36 hours. The reaction mixture was neutralized with 1N aqueous HCl, and the resulting precipitate was filtered off, washed with water and dried.The preparation of R2b was achieved using general procedure 1 starting with the preparation of R1a and methyl iodide as the alkylating agent.

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; LES LABORATOIRES SERVIER; VERNALIS (R&D) LTD; KOTSCHY, ANDRAS; WEBER, CSABA; VASAS, ATTILA; MOLNAR, BALAZS; KISS, ARPAD; MACIAS, ALBA; MURRAY, JAMES BROOKE; LEWKOWICZ, ELODIE; GENESTE, OLIVIER; CHANRION, MAIA; DEMARLES, DIDIER; IVANSCHITZ, LISA; (502 pag.)TW2018/2094; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, 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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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.

Example A4; a. Preparation of intermediate 19; A solution of l-bromo-4-chlorobutane (22.25 ml, 0.19 mol) in diethyl ether (100 ml) was added dropwise (under N2 atmosphere) to a suspension of activated Mg turnings (4.67 g, 0.19 mol) in diethyl ether (100 ml). Some crystals of iodine were also added. The temperature in the flask increased, and the orange colour turned to white. Once the addition of l-bromo-4-chlorobutane was completed, the reaction was cooled in an ice- bath and 2-naphthalenecarboxaldehyde (20.00 g, 0.13 mol) was added dropwise as a solution in THF (200 ml, dry). The reaction mixture was stirred in the ice-bath for 4 hours. Then the mixture was quenched with NH4Cl 1 N. Both phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography (eluent: n- hexane/EtOAc 20:1). The desired fractions were collected and the solvent was evaporated, yielding intermediate 19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/68272; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29671-92-9, 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. 29671-92-9, name is Carbamimidic chloride hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture consisting of S-amino-?-chloro-pyridine^-carbonitrile (4.6 g, 30 mmol), chloroformamidine hydrochloride (6.9 g , 60 mmol) and dimethylsulfon (12 g) was heated at 165 0C for 30 minutes. After cooling to room temperature, water (500 ml) was added. The solution was neutralized with a 30 % NaOH solution to pH 9-10. The precipitate was filtered off, washed with water, dried over P2O5, resulting in the pure title compound as a yellow solid (4.0 g, yield: 68 %) which was characterised as follows:- Rf = 0.40 (MeOH/CH2CI2 1 :9); and – MS (m/z): 196, 198 ([M+H]+, 100).

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; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, molecular formula is C6H3BrCl2, 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. 1435-50-3

After 1-bromo-2,5-dichlorobenzene (15.6 g, 69.1 mmol) and 2-formylphenylboronic acid (11.4 g, 76 mmol) were dissolved in tetrahydrofuran (THF) (200 mL), 2M potassium carbonate aqueous solution (70 mL) was added thereto, and tetrakistriphenylphosphino palladium (Pd(PPh3)4 (1.6 g, 2 mol%) was put thereinto, agitated and refluxed for 5 hours. The temperature was lowered to normal temperature, the water layer was removed, and the organic layer was dried with anhydrous magnesium sulfate (MgS04) and filtered. The filtered solution was concentrated under the reduced pressure, and columned with tetrahydrofuran:hexane = 1:10 to prepare the compound A-1 (13.9 g, 80%), MS: [M+H]+=251

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1435-50-3, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; EP2311826; (2011); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics