Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, 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 81927-55-1, Product Details of 81927-55-1

To a solution of (R)-Roche ester 25 (200 mg, 1.69 mmol, 1equiv) in CH2Cl2 (3 mL) was added at 0 oC benzyl trichloroacetimidate (640 mg, 2.54 mmol, 1.5 equiv). Asolution of CF3SO3H in CH2Cl2 (0.85 M, 100 muL, 0.09 mmol, 0.05 equiv) was added at 0 oC and the mixture wasstirred at room temperature for 44 h. After filtration, the filtrate was concentrated under reduced pressureand saturated aqueous NaHCO3 (15 mL) was added. The aqueous layer was extracted with EtOAc, thecombined organic layers were washed with brine, dried over MgSO4 and concentrated under reducedpressure. The crude mixture was purified by flash column chromatography (SiO2, petroleum ether/Et2O: 95/5)to afford the desired product 26 (262 mg, 74%) as a yellow oil. Rf (cyclohexane/EtOAc: 9/1, UV, KMnO4) 0.30;-8.0 (c 1.60, CHCl3); 1H NMR (CDCl3, 300 MHz) delta = 7.38 – 7.24 (m, 5H), 4.53 (s, 2H), 3.70 (s, 3H), 3.66 (dd,J 9.2, 7.3 Hz, 1H), 3.50 (dd, J 9.1, 5.9 Hz, 1H), 2.86 – 2.72 (m, 1H), 1.18 (d, J 7.1 Hz, 3H); 13C NMR (CDCl3, 75MHz) delta 175.4, 138.3, 128.5, 127.7 (2C), 73.2, 72.1, 51.8, 40.3, 14.1

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, Benzyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Echeverria, Pierre-Georges; Pons, Amandine; Prevost, Sebastien; Ferard, Charlene; Cornil, Johan; Guerinot, Amandine; Cossy, Janine; Phansavath, Phannarath; Ratovelomanana-Vidal, Virginie; Arkivoc; vol. 2019; 4; (2019); p. 44 – 68;,
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Electric Literature of 883499-24-9,Some common heterocyclic compound, 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene, 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.

In a nitrogen atmosphere, a flask containing 114 7-(diphenylamino)-9,9?-dimethyl-9H-fluoren-3-ol (100 g), 123 1-bromo-2-chloro-3-fluorobenzene (58.3 g), 77 potassium carbonate (91.5 g), and NMP (500 ml) was heated and stirred at a reflux temperature for four hours. After the reaction was stopped, the reaction liquid was cooled to room temperature, and 30 water was added thereto. A precipitate thus precipitated was collected by suction filtration. The obtained precipitate was washed with water and then with methanol and then purified by silica gel column chromatography (eluent: toluene) to obtain an intermediate 124 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (150 g).

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

Reference:
Patent; JNC CORPORATION; FUJITA, Yukihiro; (228 pag.)US2019/165279; (2019); A1;,
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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

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

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 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. 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

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

Reference 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

Application 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