Month: September 2021

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., Recommanded Product: 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

Application 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

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., HPLC of Formula: C6H3ClF2O2S

A mixture of 1.80 g (8.8 mmol) C-5, 2.29 mL (17 mmol) 2,4-difluorobenzenesulphonyl chloride, 1.07 mL (13.3 mmol) pyridine and 20 mL DCM is stirred at RT over night. 100 mL DCM is added and the reaction mixture is extracted three times with 50 mL aqueous 1M HCl. The organic layer is dried over MgSO4 and the solvent is removed under reduced pressure. The solid is dissolved in water/MeCN and further purified by RP-chromatograpy. Yield: 2.9 g (86%).

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

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. SDS of cas: 2613-32-3

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

Electric Literature of 208186-78-1,Some common heterocyclic compound, 208186-78-1, name is 1,2-Dibromo-5-chloro-3-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

Intermediate 10; 3-(2-Bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole Step A: 2-Bromo-4-chloro-6-fluoro-benzaldehyde To a solution of 1,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to -45 C. Then iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between -40 C. to -45 C. The mixture was stirred for 30 minutes at -40 C. before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between -45 C. to -20 C. After stirring for another 15 minutes at -20 C., the reaction mixture was poured into a mixture of 2N HCl (20 ml) and ether (50 ml) at 0 C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2SO4 and evaporated in vacuo to obtain the title compound as yellow solid (7.8 g, 95%).

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

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-chloro-1-fluorobenzene

To a mixture of magnesium (434 mg) and THF (2 mL) was added a slight amount of iodine under an argonatmosphere. The mixture was allowed to warm to 60C. To the mixture was added dropwise a solution of 4-bromo-2-chloro-1-fluorobenzene (3.58 g) in THF (6.5 mL) while keeping the temperature at 65C. The mixture was stirred at 60Cfor 30 minutes, and then allowed to cool to room temperature to give (3-chloro-4-fluorophenyl)magnesium bromide. Toa solution of (R)-1-(tert-butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid ethyl (2.00 g) in THF (25 mL) was added theobtained (3-chloro-4-fluorophenyl)magnesium bromide under an argon atmosphere at -40C. The mixture was stirredat -40C for 1 hour. To the reaction mixture were added a saturated aqueous solution of ammonium chloride (20 mL)and water (10 mL). The mixture was stirred at room temperature for 2 hours, and then to the mixture were added ethylacetate and water. The organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: nhexane/ethyl acetate=90/10-60/40) to give the title compound (2.79 g).

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; KONDO, Atsushi; MORITA, Naohide; ISHIKAWA, Takehiro; YOSHIDA, Masako; MORIYAMA, Akihiro; WANAJO, Isao; (158 pag.)EP3459941; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 452-83-5, The chemical industry reduces the impact on the environment during synthesis 452-83-5, name is 2-Chloro-5-fluoroaniline, I believe this compound will play a more active role in future production and life.

Nitrosonium tetrafluoroborate (802 mg, 6.87 mmol) was added to a solution of 2-chloro-5-fluoroaniline (1.00 g, 6.87 mmol) in acetonitrile (50 mL) at 0 C. The resulting mixture was stirred for 1 h, then diluted with ethyl ether (150 mL). The precipitate was filtered and air-dried to give 2-chloro-5-fluorobenzenediazonium tetrafluoroborate (1-1) as an off-white solid. 1H NMR (300 MHz, CD3OD) delta 8.66 (ddd, 1H, J=6.7, 2.1, 1.0 Hz), 8.16 (m1, 2H).

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, 2-Chloro-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fraley, Mark E.; Garbaccio, Robert M.; Hartman, George D.; Hoffman, William F.; US2006/135594; (2006); A1;,
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., HPLC of Formula: C6H3ClF2O2S

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

Reference of 7006-52-2, 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. 7006-52-2, name is N-Methyl-3-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In air, K2HPO4 (10 mol percent, 4.35mg), PMHS (242 mul), amine (0.25 mmol), formic acid (4.6equiv ,43.3mul), 18-crown-6 (20mol percent, 13.2mg) 4A MS(10mg) and 2 ml THF were added into a tube equipped with a water condenser. The reaction mixturewas stirred at 80C for 12 hours. The yields of isolated products were reported. The mixture was filtered through a silica gelcolumn with petroleum ether and ethyl acetate as the eluent. The resultant solution was concentrated and purified by silica gelcolumn chromatography to give the corresponding product.

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, N-Methyl-3-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huang, Yan; Deng, Wei; Lin, Bo-Lin; Chinese Chemical Letters; (2019);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

Roschangar et al. ,Use of lithium N,O-dimethylhydroxylamide as an efficient in situ protecting agent for aromatic aldehydes. Tertrahedron 2002, 58, 1657-1666). Preparation analogous (Nishino et al.; Process for producing 4-aminoquinazoline compound by chlorination of quinazolin-4-one or its derivative and animation. 2003) as follows: To a mixture of 6-iodo-lH-quinazolin-4-one (10) (6.8Og; 25.0 mmol), toluene (5.0 mL) and POCl3 (27.5 mmol; 2.60 mL) carefully triethylamine (27.5 mmol; 3.81 mL) was added. The mixture was heated to 80 0C for 2 h, cooled to room temperature, a solution of 3-chloro~4-(3- fluorobenzyloxy)phenylamine (15) (27.50 mmol; 6.92 g) in 2~butanone (20.0 mL) added and the mixture stirred at 80 0C for another hour. The mixture was cooled to 00C, the yellow precipitate was filtered off and added to a NaOH solution (IN; 150 mL) by stirring. After 30 min the yellow solid was filtered off, washed with water and a small amount of acetone and dried in vacuo. Yield (8.38 g; 66%) analytical pure sample. 1H-NMR (DMSO-[D6]): delta (ppm) = 5.26 (s, 2H), 7.15-7.22 (m, IH), 7.27 (d, IH, J = 9.1 Hz), 7.29-7.35 (m, 2H), 7.43-7.51 (m, IH), 7.56 (d, IH, J = 8.8 Hz), 7.74 (dd, IH, J = 9.1 Hz, 4J = 2.5 Hz), 8.02 (d, IH5 4J = 2.5 Hz), 8.12 (dd; IH, J = 8.8 Hz, 4J = 1.7 Hz)5 8.62 (s, IH), 8.96 (d, 4J = 1.7 Hz), 9.90 (s, IH, exchangeable).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; 4SC AG; WO2009/63054; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics