Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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 19752-55-7, category: chlorides-buliding-blocks

Example S.3: Synthesis of 3,5-dichloro-2,2,2-trifluoro acetophenone (Compound example no.2 of table C.1 ); To 5.1 g (0.209 mol) Magnesium turnings was added 0.45 g of a 1 molar solution of DIBAL in hexane at 6O0C. After 15 min, 3,5-dichloro-bromobenzene (5.0 g, 0.022 mol) and 25 mL THF were added and the mixture was stirred. After start up of the reaction a mixture of 45g (0.2 mol) 3,5-dichloro-bromobenzene and 250 mL THF was added under reflux. After completion of the reaction the mixture was cooled to 00C and 31.1 g (0.219 mol) ethyl trifluoroacetate was added. After 2 h an aqueous solution of NH4CI was added an the mixture was separated between MTBE and aqueous NH4CI solution. The organic layer was separated and the solvent was removed in vacuum. (34.3g brown oil; purity 70percent ace. to g.c; yield 50percent)1H-NMR (360 MHz, CDCI3): delta = 7.7 (s, 1 H), 7.9 (s, 2H) ppm.

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; BASF SE; Rack, Michael; Koerber, Karsten; WO2010/125130; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl 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. HPLC of Formula: C8H9ClO4S

A solution of 2,4-dimethoxybenzene-1-sulfonyl chloride (0.67 g, 2.8 mmol) and methyl 3-aminobenzo[d]isoxazole-6-carboxylate A9 (0.55 g, 2.8 mmol) in pyridine (4 ml.) was irradiated in the microwave at 130 C for 3 hours. The reaction was cooled to room temperature then diluted with DCM (40 ml_). The organics were washed with 1 M HCI (40 ml.) and the aqueous layer back-extracted with DCM (2 x 40 ml_). The combined organic layers were dried in vacuo and the residue purified twice by column chromatography (24 g S1O2 cartridge, 0-35% EtOAc in petroleum benzine 40- 60 C) [200] to give two batches of the title compound (0.369 g, impure and 0.0310 g, 2.8% yield, >95% purity) as white solids. 1H NMR (400 MHz, methanol-c/4) d 8.13 – 8.06 (m, 2H), 7.97 (dd, J = 1.25, 8.47 Hz, 1H), 7.86 – 7.80 (m, 1H), 6.58 (dq, J = 2.29, 4.60 Hz, 2H), 3.95 (s, 3H), 3.83 (s, 3H), 3.79 (s, 3H). LCMS: rt 3.26 min, m/z 392.8 [M+H]+, 415.8 [M+Na]+.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); 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 60811-21-4 as follows. Formula: C6H3BrClF

2,5-Dimethoxyacetophenone (8.1 g, 45.1 mmol) and l-bromo-3-chloro-4-fluorobenzene (9.4 g, 45.1 mmol) were added to a mixture of tris(dibenzylideneacetone)dipalladium(0) (620 mg, 0.68 mmol), 2,2′-bis(diphenylphosphino)-l, -binaphthalene (1012 mg, 1.63 mmol), sodium tert-butoxide (5.9 g, 61.7 mmol), and THF (110 mL). After degassing with three vacuum/N2 cycles, the mixture was stirred at 70 C overnight, allowed to cool to rt, diluted with water, and extracted with ether (x 2). The combined organic extracts were washed with brine, dried (Na2S04), filtered, concentrated, and purified by silica gel chromatography (0-15% EtOAc in hexanes) to give 4.7 g of 2-(3-chloro-4-fluorophenyl)-l-(2,5-dimethoxyphenyl)ethanone as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 7.44 (dd, 1H), 7.36-7.31 (m, 1H), 7.23-7.19 (m, 1H), 7.14-7.11 (m, 3H), 4.29 (s, 2H), 3.86 (s, 3H), 3.72 (s, 3H).

According to the analysis of related databases, 60811-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; HAGER, Jeffrey, H.; CHOW MANEVAL, Edna; WO2014/205136; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, molecular formula is C6H3BrClF, 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. COA of Formula: C6H3BrClF

A suspension of 1-bromo-2-chloro-4-fluorobenzene (4.19 g, 20 mmoles), piperazine (10.32 g, 120 mmoles), sodium tert-butoxide (2.3 g, 1.5 mmoles), tris(dibenzylideneacetone)dipalladium (366 mg, 0.4 mmoles) and racemic (-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (747 mg, 1.2 mmoles) in toluene (2 mL) was heated to 120 C. overnight. The mixture was cooled, filtered and the filtrate concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-5% 2N methanolic ammonia in DCM) to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110407-59-5, its application will become more common.

Reference:
Patent; Link, James T.; Chen, Yixian; Jae, Hwan-Soo; Patel, Jyoti R.; Pliushchev, Marina A.; Rohde, Jeffrey J.; Shuai, Qi; Sorensen, Bryan K.; Winn, Martin; Wodka, Dariusz; Yong, Hong; US2005/277647; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1127-85-1, 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. 1127-85-1 name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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.

To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazolin (7.00 g, 34.5 mmol) in THF (70 ml_) was added 50% aqueous MeNH2 (7.77 g, 86.2 mmol). The mixture was stirred at ambient temperature for 2.25 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (NH-silica, 20% EtOAc in hexane) to give (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyl-amine (6.08 g, 83%) as a white solid. ESI MS m/e 234, M + Na+; 1H NMR (300 MHz, CDCI3) 8 1.62-1.90 (m, 4 H), 2.59 (t, J= 6.0 Hz, 2 H), 2.76 (t, J= 6.6 Hz, 2H), 3.06 (s, 6 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, and friends who are interested can also refer to it.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, 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. SDS of cas: 50594-82-6

d. 1,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene A mixture of 3,4,5-trichloro-alpha,alpha,alpha-trifluorotoluene (10 g. 0.04 mol), and the dipotassium salt of 1,3-dihydroxybenzene (4 g. 0.021 mol) in 150 ml. sulfolane is stirred and heated 70 minutes at ~120 C. The cooled reaction mixture is diluted with benzene (350 ml.) and washed once with water (1 L). Hexane (200 ml.) is added, and the solution washed with water (3*500 ml.) dried, filtered through activated silica gel (~25 g.), and the solvents removed. The residual oil is crystallized from a mixture of pentane and benzene to give 1,3-bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene (5.3 g. 49%) m.p. 121-122 C.

The synthetic route of 3,4,5-Trichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US31455; (1983); E1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 103724-99-8,Some common heterocyclic compound, 103724-99-8, name is 2-Bromo-5-chloro-1,3-dimethylbenzene, molecular formula is C8H8BrCl, 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 bromo(4-chloro-2,6-dimethylphenyl)magnesium, prepared at 30-35 C. from 50 mmol of 4-chloro-2,6-dimethylbromobenzene, 1 mmol of bromo(4-chloro-2,6-dimethylphenyl)magnesium (to start the Grignard synthesis) and 55.5 mmol of magnesium in 50 ml of tetrahydrofuran, were added 5 mmol of copper(I) iodide. Then, 48 ml of a 2.5-3.3 molar solution of ethylene oxide in tetrahydrofuran (120 mmol, calculated for a concentration of 2.5 M) were metered in at 20 C. over the course of 30 minutes. After 16 hours at 20 C., the reaction mixture was placed on 100 g of ice and adjusted to pH 1 with sulphuric acid. After triple extraction with in each case 50 ml of methylene chloride, the combined organic phases were extracted once by shaking with 30 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator. There remained an oil, in which, according to GC/MS analysis, the ratio of 2-(4-chloro-2,6-dimethylphenyl)ethanol to 1-(4-chloro-2,6-dimethylphenyl)ethanol was >99:1. GC/MS: m/e=184 (M+ (35Cl), 25%), 153 (35Cl, 100%). 1H-NMR (600 MHz, d-DSMO): delta=2.28 (s, 6H), 2.75 (m, 2H), 3.45 (m, 2H), 4.74 (m, 1H), 7.0 (s, 2H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-chloro-1,3-dimethylbenzene, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; HIMMLER, Thomas; BRUeCHNER, Peter; (7 pag.)US2019/23633; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, 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. Recommanded Product: 2,4,5-Trifluorobenzene-1-sulfonyl chloride

EXAMPLE 293 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)(methyl)amino)-2,5-difluoro-//-(thiazol-4- yl)benzenesulfonamide 2,2,2-trifluoroacetate Step 1. Preparation of te/f-butyl thiazol-4-yl((2,4,5-trifluorophenyl)sulfonyl)carbamate To a solution of terf-butyl thiazol-4-ylcarbamate (1.47 g, 7.35 mmol) in anhydrous tetrahydrofuran (10 mL) was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (10.3 mL, 10.3 mmol) at -78 C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. The reaction mixture was then cooled to -78 C, and a solution of 2,4,5- trifluorobenzenesulfonyl chloride (1.22 mL, 8.82 mmol) in anhydrous tetrahydrofuran (10 mL) was added to it. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h. The mixture was diluted with ethyl acetate (50 mL), washed with saturated ammonium chloride (2 chi 30 mL), brine (2 chi 30 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and purification of the residue by column chromatography, eluting with a gradient of 0 to 50% of ethyl acetate in hexanes, provided the title compound as a colorless solid (2.0 g, 68% yield): MS (ES+) m/z 395.0 (M + 1).

The synthetic route of 220227-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BURFORD, Kristen, Nicole; CHOWDHURY, Sultan; COHEN, Charles, Jay; DEHNHARDT, Christoph, Martin; DEVITA, Robert, Joseph; EMPFIELD, James, Roy; FOCKEN, Thilo; GRIMWOOD, Michael, Edward; HASAN, Syed, Abid; JOHNSON, James, Philip, Jr.; ZENOVA, Alla, Yurevna; (493 pag.)WO2017/201468; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 67279-24-7, A common heterocyclic compound, 67279-24-7, name is 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, molecular formula is C8H8Cl2N2, 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 l,4-dichloro-5,6,7,8-tetrahydro-phthalazine (0.50 g, 2.46 mmol) in THF (5 mL) are added 4-fluoro-benzyl zincchloride (0.5M in THF) (6.40 mL, 3.20 mmol) and palladium tetrakis triphenylphosphine (0.36 g, 0.31 mmol). The mixture is degassed and stirred at 500C overnight. Then the reaction mixture is cooled down to room temperature, sat. NaHCO3 and water are added and the mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by chromatography (EtOAc/Hexane: 10% – 40%) to give l-chloro-4-(4-fluoro-benzyl)-5,6,7,8-tetrahydro-phthalazine (compound 1Of) (0.51g, 30%). m/z =277.11 [M+l]

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; NOVARTIS AG; WO2008/110611; (2008); 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

2,4-Dichloro-5,6,7,8-tetrahydroquinazoline(103 mg, 0.640 mmol) and K2CO3 (265 mg, 1.92 mmol) were dissolved in DMF (3.2 ml), and then 3-fluorobenzenethiol (110 mg, 0.767 mmol) was slowly added dropwise and stirred at room temperature for 2 hours .After confirming the termination of the reaction, the reaction solution was diluted with dichloromethane and extracted several times with distilled water. The separated organic layer was dried over anhydrous MgSO4, filtered under reduced pressure, and concentrated.The concentrated filtrate was separated and purified by silica gel column chromatography (Hex: EtOAc = 18: 1) and purified to obtain the desired compound (181 mg, 96%) as a white solid.

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; Nam, Ghil-Soo; Choo, Hyun-Ah; Choi, Kyung-Il; (40 pag.)KR101730790; (2017); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics