Month: February 2021

Related Products of 118754-53-3, The chemical industry reduces the impact on the environment during synthesis 118754-53-3, name is 4-Bromo-3,5-dichlorobenzotrifluoride, I believe this compound will play a more active role in future production and life.

Stille Coupling Procedure: 1-Bromo-2,6-dichloro-4-trifluoromethylbenzene(3; 1.205 g, 4.1 mmol) and tributylvinyltin (1.268 g, 4 mmol)were degassed with argon. Toluene (15 mL) was then added, degassed,and stirred. Pd(PPh3)4 (0.173 g, 0.15 mmol) was added and themixture was refluxed for 24 h. The crude product was concentratedby rotary evaporation and purified by silica gel column chromatographywith hexanes to give a colorless oil; yield: 0.562 g (57%).1H NMR (400 MHz, CDCl3): delta = 7.58 (s, 2 H), 6.70 (dd, J = 18, 12 Hz, 1H), 5.86 (dd, J = 17, 1.1 Hz, 2 H), 5.82 (dd, J = 12, 1.1 Hz, 2 H).13C NMR (100 MHz, CDCl3): delta = 138.6, 134.9, 130.6 (q, J = 34 Hz),130.0, 125.3 (q, J = 3.8 Hz), 124.4, 122.6 (q, J = 271 Hz).Anal. Calcd for C9H5Cl2F3: C, 44.85; H, 2.09. Found: C, 45.00; H, 2.25.

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, 4-Bromo-3,5-dichlorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Miller, Daniel K.; Bailey, Christopher A.; Sammelson, Robert E.; Synthesis; vol. 47; 18; (2015); p. 2791 – 2798;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described 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, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); 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. 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Computed Properties of C6H2ClF3O2S

General procedure: To a solution of 500 mg of 6-(4-amino-phenyl)-1H-pyrazolo[3,4-b]pyrazin-3-ylamine hydrochloride and 397 mg of 2-fluoro-5-methyl-benzenesulfonyl chloride in 4 ml DCM, 0.16 ml pyridine were added and the reaction mixture was stirred for 16 h at RT. Then, the solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/EtOAc. The fractions containing the product were combined and the solvent evaporated under reduced pressure. The title compound was prepared by adapting the procedures described in example 19, employing 2,4,5-trifluoro-benzenesulfonyl chloride instead of 2-fluoro-5-methyl-benzenesulfonyl chloride. MS (ES+): m/e = 421.1 (M+H).

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; SANOFI; Nazare, Marc; Halland, Nis; Schmidt, Friedemann; Weiss, Thilo; Hofmeister, Armin; EP2570415; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 14862-52-3, 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. 14862-52-3 name is 3,5-Dibromochlorobenzene, 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.

Synthesis of compound (1-1) Intermediate (A-1): Synthesis of N^N’.N’-Tetrakis-biphenyl^-yl-S- chloro-benzene-1,3-diamine Tri-ieri-butylphosphine (11.1 mL of a 1.0 M solution in toluene, 11.1 mmol), palladium acetate (1.25 g, 5.55 mmol) and cesium carbonate (75.0 g, 232 mmol) are added to a solution of bis-biphenyl-4-yl-amine (CAS Nr. 102113- 98-4) (59.0 g, 185 mmol) and ,3-Dibromo-5-chloro-benzene (25 g, 92 mol) in degassed toluene (600 ml), and the mixture is heated under reflux for 2 h. The reaction mixture is cooled to room temperature, extended with toluene and filtered through Celite. The filtrate is evaporated in vacuo, and the residue is crystallised from heptane/toluene. Yield: 67.7g, 75%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dibromochlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; MUJICA-FERNAUD, Teresa; MONTENEGRO, Elvira; PFISTER, Jochen; (103 pag.)WO2016/78738; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 261762-56-5, 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 261762-56-5 as follows.

To a mixture of 1-chloro-2-fluoro-3-methoxy-benzene (5.00 g, 31.1 mmol) in dichloromethane (40 mL) was added titanium tetrachloride (10.0 g, 52.9 mmol) dropwise at 0 C under nitrogen. Dichloro(methoxy)methane (3.58 g, 31.1 mmol) was then added to the solution. Then the mixture was stirred at rt for 3 hours. On completion, the residue was poured into ice- water (50 mL) and extracted with ethyl acetate (50 mL). The combined organic layer was washed with brine (50 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with petroleum ether/ethyl acetate (20/1 to 3/1) to give the title compound. ?HNMR (400 IVIFIz, DMSO-d6) = 10.15 (s, 1H), 7.74 (d, J6.8 Hz, 1H), 7.37 (d, J 6.0 Hz, 1H), 3.98 (s, 3H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (163 pag.)WO2017/156179; (2017); 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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1303587-99-6

Synthesis of 8-benzyl-2-chloro-7 , 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0457] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (100 mg, 0.58 mmol) in DMF (3.5 mL) under argon atmosphere were added sodium hydride (28 mg, 1.16 mmol) and bromomethylbenzene (216 mg, 1.16 mmol) at 0 C. The reaction mixture was warmed to RT and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 40% EtOAc:hexane to afford 8-benzyl-2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (120 mg, 75%) as an off-white solid. 1H-NMR (DMSO-<, 500 MHz): delta 7.62 (s, 1H), 7.30-7.20 (m, 5H), 4.10-4.08 (m, 2H), 3.78 (t, 2H), 3.49-3.47 (m, 2H), 2.88 (t, 2H); LCMS: 275.8 (M+); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.64 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.6). 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 1303587-99-6. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-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.

Toluene (250 g) and water (150 g) were added to 50.0 g (0.34 mol) of 3-chloro-4-fluoroaniline and the mixture was heated to 60 C. Into this reaction mixture was added dropwise 50.7 g (0.36 mol) of benzoyl chloride. At the same time, a 10% aqueous sodium hydroxide solution was added dropwise thereto to maintain the pH around 8. After the dropwise addition was completed, the mixture was stirred for 2 hours and cooled in ice. The precipitate was filtered, washed with water, and dried to obtain 74.8 g of the title compound (yield: 87%) as a white solid. 1H-NMR (CDCl3, deltappm) 7.11-7.18 (2H, m), 7.50-7.61 (3H, m), 7.88-7.90 (2H, m), 8.05 (1H, brs), 8.38-8.42 (1H, m).

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; MITSUI CHEMICALS AGRO, INC.; Kitajima, Kazuki; Kodaka, Kenji; Katsuta, Hiroyuki; Okumura, Kunio; US2013/317247; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, 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. name: 1-(2-Chloroethyl)azepane hydrochloride

To a solution of 2,2-bis(4-hydroxyphenyl)methylenecyclohexane (23.3 mg, 83.1 mumol) in DMF (0.83 mL) at 0 ¡ãC was added 55percent sodium hydride (dispersion in paraffin liquid, 29.1 mg, 0.667 mmol). The reaction mixture was stirred for 30 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (54.5 mg, 0.275 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 4 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 15/1) to afford RID-F-S*16 (compound 14) (32.0 mg, 73percent) as a yellow oil

The synthetic route of 1-(2-Chloroethyl)azepane hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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. Formula: C6H4ClN3

General procedure: A typical procedure for the catalytic N-sulfonylation of benzotriazoles using I2 as catalyst includes: in EtOAc-H2O (10:1) mixture solvent (2 mL), benzotriazole 1a (0.3 mmol), sodium benzenesulfinate 2a (0.9 mmol), I2 (0.06 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 3 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3 (8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3* 5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (petroleum ether/ethyl acetate = 3:1, v/v) to furnish 1-phenylsulfonylbenzotriazole 3a [28] in 97% yield.

The synthetic route of 94-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Si-Xue; Zhang, Yi-Kun; Shi, Hong-Wei; Yan, Jie; Chinese Chemical Letters; vol. 27; 9; (2016); p. 1519 – 1522;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 110407-59-5, A common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, molecular formula is C6H3BrClF, 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.

Step C: Preparation of a-(2-chloro-4-fluorophenyl)-2 -methyl- 1 -(2,4,6- trifluorophenyl)- lH-imidazole-5 -methanolTo a mixture of l-bromo-2-chloro-4-fluorobenzene (2.35 mL, 19.3 mmol) in tetrahydrofuran (15 mL) at -2 to -3 C was added isopropylmagnesium chloride lithium chloride (1.3 M in tetrahydrofuran, 15 mL, 19.5 mmol) dropwise over ten minutes. The reaction mixture was stirred for 1.5 h at 0 to 5 C, and then 2 -methyl- 1 -(2,4,6- trifluorophenyl)-lH-imidazole-5-carboxaldehyde (i.e. the product of Step B) (2.32 g, 9.65 mmol) in tetrahydrofuran (8 mL) was added dropwise over 10 minutes while maintaining the reaction temperature at about 0 to 5 C. After 1 h, saturated aqueous ammonium chloride solution (10 mL) was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate (2 x 25 mL). The combined organic layers were washed with aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure at 45 C until a slurry was obtained. Hexanes were added to the resulting slurry (with agitation) and the mixture was allowed to cool to ambient temperature (about 20 C). The resulting precipitate was collected on a sintered glass frit funnel, washed ethyl acetate/hexanes (1 : 1, 3 mL), and allowed to air dry to provide the title compound, a compound of the present invention, as a tan solid (1.866 g)..H NMR (DMSO- ) delta delta 7.5 (m, 3H), 7.38 (m, 1H), 7.20 (m, 1H), 6.43 (s, 1H), 5.96 (m, 1H), 5.64 (m, 1H), 2.05 (s, 3H).

The synthetic route of 110407-59-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; BEREZNAK, James, Francis; KAR, Moumita; TAGGI, Andrew, Edmund; CHEN, Yuzhong; WO2012/44650; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics