Month: June 2021

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. 106-39-8, name is 1-Bromo-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-4-chlorobenzene

General procedure: To a round bottle with a magnetic stir bar, ligand (0.01% mmol), PdCl2 (0.01% mmol), aryl halides (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol) and 6 ml of solvent were added. The reaction mixture was conducted at room temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20:1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhou, Zhen; Cao, Gao; Liu, Ning; Chemistry Letters; vol. 48; 6; (2019); p. 547 – 550;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 51114-68-2, 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. 51114-68-2, name is 3-Chloro-2-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 40; This Example. illustrates the preparation of(2-chloro-6-{4-[4-(3,4-dichloro- phenoxy)-piperidin-1-ylmethyl]-piperidin-1-yll-phenoxy)-acetic acid; To a solution of 4-[4-(3,4-dichloro-phenoxy)-piperidin-1-ylmethyl]-cyclopentane- 1,2-diol (0.54 g) in dichloromethane (20 mL), was added lead tetraacetate (0.99 g) and potassium carbonate (0.25 g). The mixture was stired at room temperature for 1.5 h, then 3-chloro-2-methoxy-aniline (0.26 g) and sodium triacetoxyborohydride (0.64 g) were added. After a further 2 h the mixture was partitioned between dichloromethane and sodium hydrogen carbonate solution (sat. ) and the organics were dried over sodium sulfate. Concentration in vacuo gave a brown gum, that was taken up in dichloromethane (20 mL) and treated dropwise with boron tribromide (1.0 M soln in dichloromethane, 12.4 mL) and stirred at RT for 1 h. The reaction was diluted with methanol (100 mL) and concentrated in vacuo. The residue was partitioned between ethyl acetate and sodium hydrogen carbonate solution (sat. ) and the organics were dried over sodium sulfate and concentrated in vacuo. The residue was subject to reversed phase HPLC (Xterra column, eluting 50% to 95% acetonitrile in aqueous ammonia (0.2%) ), yielding 2-chloro-6-{4-[4-(3,4-dichloro- phenoxy)-piperidin-1-ylmethyl]-piperidin-1-yl]-phenol (0.12 g). The phenol was dissolved in DMF (5 mL) ; potassium carbonate (0.03 g) and methyl bromoacetate (0.15 g) were added. The reaction was heated at 70 C for 2 h and then partitioned between sodium hydrogen carbonate solution (sat. ) and diethylether. The organics were dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in THF:water (1:1,5 5 mL) and lithium hydroxide (0.02 g) was added. The reaction was stirred at RT for 1 hr and then concentrated in vacuo. The residue was dissolved in water (5 mL) and neutralised with the dropwise addition ofHCl (1 M) to precipitate the title compound (0.03 g) as a white solid which was collected by filtration. ¹H NMR No. (DMSO) (d, 1H), 7.26 (d, 1H), 7.14 – 6.95 (m, 4H), 4.57 (s, 2H), 4.49 – 4.39 (m, 1H), 2.75 – 2.55 (m, 2H), 2.49 – 2.36 (m, 2H), 2.29 – 2.16 (m, 4H), 2.00 – 1.87 (m, 2H), 1.86 – 1.73 (m, 2H), 1.67 – 1.54 (m, 2H), 1.32 – 1.14 (m, 2H), 3.57 – 3.13 (m, 3H); MS [M-H] -=525/527 (APCI-).

The synthetic route of 3-Chloro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/97775; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 round bottle, isopropanol (20 mL), 3-bromoaniline (0.62 g, 3.6 mmol), 4-cholo-6-iodo-quinazoline 15 (0.87 g, 3 mmol) andtriethylamine (0.36 g, 3.6 mmol) was added. The resulting reactionmixture was stirred at room temperature for 6 h and then at refluxfor another 3 h. After cooling to room temperature, the yellow solidwas collected by suck filtration, wash with isopropanol, water andether sequentially, and dried at 50 C to afford compound 12a as ayellow solid (0.74 g, 69% yield)

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Songwen; Li, Yingbo; Zheng, Yufen; Luo, Laichun; Sun, Qi; Ge, Zemei; Cheng, Tieming; Li, Runtao; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 442 – 458;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 220227-21-4, These common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-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.

General procedure: To a solution of /V-(2,4-dimethoxybenzyl)-1 ,3,4-thiadiazol-2-amine (1.09 g, 4.30 mmol) in tetrahydrofuran (20 mL) was added lithium /)/’s(trimethylsilyl)amide (4.3 mL of a 1 M solution in tetrahydrofuran, 4.3 mmol) at -78 C. The reaction mixture was allowed to stir for 30 minutes at 0 C and a solution of 2,4,5- trifluorobenzenesulfonyl chloride (0.99 g, 4.3 mmol) in tetrahydrofuran (10 mL) was added dropwise at -78 C. After the addition was complete, the cooling bath was removed. The reaction mixture was stirred for 3 h at ambient temperature and saturated aqueous ammonium chloride (10 mL) was added. The resulting mixture was extracted with ethyl acetate (2 x 30 mL). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford /V-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-/v’-(1 ,3,4- thiadiazol-2-yl)benzenesulfonamide in 57% yield (1.10 g) as a colorless solid: MS (ES+) m/z 446.0 (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.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella; WO2013/64983; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, molecular formula is C6H4ClF2N, 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. Safety of 2-Chloro-4,5-difluoroaniline

Lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahydrofuran, 42 mmol, CAS No 4039-32-1 ) was added drop wise within 5 minutes to a solution of 2-chloro-4,5-difluoroaniline (3.88 g, 23.2 mmol) in tetrahydrofuran (1 10 ml) at -78 C and the mixture was stirred for 1 h at that temperature. A solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (10.0 g, 21 .1 mmol) in tetrahydrofuran (1 10 ml) was added and the mixture was stirred for 2 h at -78(C. The mix ture was warmed to room temperature and stirred for 4 d. For work-up, the reaction mixture was added to a mixture of water and sodium bicarbonate solution and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washed with sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate). The product containing fractions were concentrated and were purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate) to give the title compound in 2 fractions: fraction 1 (7.53 g, single isomer based on1H NMR, isomer 1, contains impurities from aniline and isomer 2), fraction 2 (1 .13 g, isomer 2). Fraction 1 (isomer 1 ):1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.67-7.55 (m, 5H), 7.52-7.30 (m, 9H), 3.97 (br s, 1H), 3.60 (t, 2H), 2.15-2.07 (m, 2H), 2.04 (t, 2H), 1 .76-1 .63 (m, 2H), 1 .58-1 .45 (m, 2H), 1 .39-1 .27 (m, 2H), 1 .05 (s, 9H). LC-MS (Method 1 ): Rt= 1 .80 min; MS (ESIpos): m/z 518.3 [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 2613-32-3, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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 4584-46-7, Safety of 2-Chloro-N,N-dimethylethanamine hydrochloride

The experimental equipment used in this study was a Vapourtec R4/R2+ flow reactor. Stock A: Ginkgolide B (4.4g), acetonitrile (100mL). Stock B: DECH (2.15g), potassium iodide (0.332g), acetonitrile (90mL), water (10mL). Initially, two flows were pumped into micromixer LH 25. Upon mixing together, the mixture entered the packed bed microreactor filled with acid-binding agents. The total volume of the packed bed microreactor was 24.5mL. However, the remaining volume was 4.5mL when the microreactor was filled with calcium carbonate (2.5g). The volumetric flow rate of stock A/B was 0.75mL/min. That is to say, the residence time in the microreactor was 3min. Upon completion at a set temperature for the appropriate residence time, the obtained organic layer was concentrated under vacuum and further purified by column chromatography on silica gel (MeOH/CH2Cl2=1:50). Dimethylaminoethyl ginkgolide B: 1H NMR (DMSO-d6, 300MHz): delta 7.12 (s, 1H), 6.32 (s, 1H), 6.12 (s, 1H), 5.31 (d, 1H, J=3.6Hz), 5.12 (s, 1H), 4.54 (d, 1H, J=7.5Hz), 4.35-4.41 (m, 1H), 4.07 (d, 1H, J=7.2Hz), 3.55-3.59 (m, 1H), 2.81-2.88 (m, 1H), 2.57-2.64 (m, 1H), 2.32 (d, 1H, J=12.6Hz), 2.18 (s, 6H), 2.11-2.12 (m, 1H), 1.83-1.94 (m, 1H), 1.71-1.77 (m, 1H), 1.11 (d, 3H, J=6.9Hz), 1.04 (m, 9H). 13C NMR (DMSO-d6, 300MHz): delta 176.44, 173.02, 170.18, 109.59, 98.40, 92.78, 82.00, 78.62, 74.36, 74.00, 72.19, 67.52, 64.11, 57.44, 48.64, 43.71, 41.62, 40.09, 39.81, 39.53, 39.25, 38.98, 36.57, 31.75, 28.58. HRMS calcd. for C24H33NO10 496.2177 [M+H], found 496.2196.

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:
Article; Qin, Yin-Lin; He, Wei; Su, Mei; Fang, Zheng; Ouyang, Ping-Kai; Guo, Kai; Chinese Chemical Letters; vol. 27; 10; (2016); p. 1644 – 1648;,
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. 85462-59-5, name is 2-Bromo-5-chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-5-chloro-4-fluoroaniline

Step 1. Methyl trans-2-Amino-4-chloro-5-fluorocinnamate The title compound was prepared according to the procedure described in step 1 of Example 133 from 2-bromo-5-chloro-4-fluoroaniline (JP 01311056 A2, Nippon Kayaku Co., Ltd., Japan). 1H-NMR (CDCl3) delta: 7.69 (1H, d, J=15.8 Hz), 7.15 (1H, d, J=9.7 Hz), 6.74 (1H, d, J=6.4 Hz), 6.31 (1H, d, J=15.8 Hz), 3.81 (3H, s).

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; Nakao, Kazunari; Stevens, Rodney William; Kawamura, Kiyoshi; Uchida, Chikara; Koike, Hiroki; Caron, Stephane; US6608070; (2003); B1;,
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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Difluorobenzene-1-sulfonyl chloride

A mixture of 75 mg (0.22 mmol) E-7, 59 muL (0.44 mmol) 2,4-difluoro-benzenesulfonyl chloride and 56 muL (0.71 mmol) pyridine in 3 mL DCM is stirred over night at RT. The reaction mixture is concentrated under reduced pressure and the residue is purified by RP chromatography (C18, 20-90% acetonitrile in water containing 0.1% formic acid). Yield: 52 mg (46%). HPLC-MS: M+H = 516; tR = 1,17 min.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 104-11-0, 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. 104-11-0 name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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.

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2845-89-8,Some common heterocyclic compound, 2845-89-8, name is 1-Chloro-3-methoxybenzene, molecular formula is C7H7ClO, 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: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20-100muL, 0.01-0.05 mol%, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.

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

Reference:
Article; Liu, Feng; Hu, Yuan-Yuan; Li, Di; Zhou, Quan; Lu, Jian-Mei; Tetrahedron; vol. 74; 39; (2018); p. 5683 – 5690;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics