Month: May 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. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3Cl3

Example 1; Method A-1; Preparation 2-bromo-1-(2, 4, 6-trichlorophenyl) ethanone; A mixture of 1,3, 5-trichlorobenzene (10.0 g, 55.1 mmol), 2-bromoacetyl bromide (5.0 mL, 57.8 mmol, 1.05 eq), and aluminum chloride (7.7 g, 57.8 mmol, 1.05 eq) was heated neat at 80 C under argon for 17 h until a black precipitate is formed. The reaction was cooled to room temperature, and the resultant black mass was dissolved in ethyl acetate (500 mL). Water (200 mL) was added slowly at 0 C to quench the reaction, and the biphasic layers were separated. The organic layer was then washed with water (2 x 150 mL) and brine (1 x 150 mL), dried (MgS04), filtered, and evaporated in vacuo. Recrystallization from hexane gave 11.5 g (69.3%) of 2-bromo-1-(2, 4, 6-trichlorophenyl)- ethanone as a fluffy white solid. 1H-NMR (DMSO-d6) 6 7.86 (s, 2H), 4.78 (s, 2H); Rf = 0.28, 2% ethyl acetate-hexane.

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2003/72561; (2003); A1;,
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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: 13918-92-8

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

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:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
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Related Products of 1435-48-9, 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. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add NaH (60% in mineral oil, 0.132 g, 3.32 mmol) to 1- (benzyl-methyl-amino)-4-methyl-3-ol (0.498 g, 2.21 mmol) in anhydrous DMSO (10 mL). After 30 minutes, add 1, 3-dichloro-4- fluorobenzene (0.474 g, 2.87 mmol) and then heat the reaction mixture at 60C overnight. Cool the mixture and partition between EtOAc and water. Separate the layers and extract the aqueous layer with EtOAc. Combine the organic extracts, wash with aqueous saturated sodium chloride solution, dry over anhydrous Na2SO4, filter, and concentrate in vacuo. Purify the residue on silica gel eluting with 5% 2N NH3 in MeOH/dichloromethane to give benzyl- [3- (2, 4-dichloro- phenoxy) -4-methyl-pentyl] -methyl amine (0.385 g, 48%). Mass spectrum (ion spray): m/z = 366 (M+1),’H NMR (CD30D) 8 734 (d, 1H), 7.28-7. 17 (m, 6H), 7.06 (d, 1H), 4.35-4. 31 (m, 1H), 3.48 (dd, 2H), 2.55-2. 43 (m, 2H), 2.19 (s, 3H), 1.98-1. 83 (m, 3H), 0.98 (dd, 6H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/92835; (2005); A1;,
Chloride – Wikipedia,
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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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2106-02-7

In another 1L four-neck reaction flask, under the protection of nitrogen, 219.54 g of tetrahydrofuran was added in sequence.77.43g (0.532mol) 2-chloro-4-fluoroaniline, 0.73g (0.00532mol) zinc chloride, 0.29g (0.000532mol) (dppp)NiCl2, stirring, the reaction system is cooled to 10 ~ 15 C, dripping Add the 3,4-dichlorophenylmagnesium bromide Grignard reagent produced in step 1 to the system, keep the temperature at 10-15 C, add the dropwise time for 3 hours, add dropwise, and keep warm for 4 h.After the sampling and detection reaction was completed, dilute hydrochloric acid was added dropwise to the reaction liquid, the reaction was quenched, stirred for 10 min, allowed to stand, layered, and the organic layer was washed with a 5% sodium chloride solution.The mixture was allowed to stand for stratification, and the organic layer was added with activated carbon, heated to reflux, filtered while hot, and the filtrate was concentrated under reduced pressure to remove tetrahydrofuran.So far, the temperature was lowered to 20 to 25 C to obtain a white flake solid, which was 3′,4′-dichloro-5-fluoro-2-aminobiphenyl, and the solid was weighed to 123.4 g, and the yield was 90.6% (by 2- Chloro-4-fluoroaniline), purity (GC) ? 99.0%.

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; Lianhua Science And Technology (Shanghai) Co., Ltd.; Lianhua Technology Co., Ltd.; Liaoning Tian Yu Chemical Co., Ltd.; Hubei Jun Tai Pharmaceutical And Chemical Co., Ltd.; Fan Xiaobin; Guo Zhanghong; Jiang Peng; (18 pag.)CN105198682; (2018); B;,
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Electric Literature of 1005-56-7, A common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

The compound 24 (0.75 g, 1.75 mmol) was dissolved in anhydrous dichloromethane (20 mL) and phenyl chlorothionoformate (0.356 mL, 2.62 mmol) was added slowly at 0 C. After added pyridine (1.0 mL) the reaction mixture was stirred at for overnight and concentrated. The crude product was purified using silica gel column chromatography (10% EtOAc in Hexane) to give of desired 25 (0.94 g, 95%). 13C NMR (150MHz, CDCl3): d 166.19, 153.17, 133.79, 133.25, 130.04, 129.94, 129.75, 128.75, 128.53, 126.85, 122.08, 114.07, 101.34, 85.06, 80.07, 79.46, 78.88, 62.93, 26.29, 25.16.

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:
Article; Yu, Hai; Cao, Hongzhi; Tiwari, Vinod Kumar; Li, Yanhong; Chen, Xi; Bioorganic and Medicinal Chemistry Letters; vol. 21; 17; (2011); p. 5037 – 5040;,
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Electric Literature of 13526-66-4, 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 13526-66-4 as follows.

Example 1 (£)-2-(1-(3-((7-Fluoroquinolin-6-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene)- hydrazinecarboxamide6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-(7-f luoro-quinolin-6-yl)-methanol (1.1 ) To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (13.27 g, 57.1 mmol) in 160 ml of THF was added EtMgBr (68.5 ml, 68.5 mmol) solution at room temperature. The reaction mixture was stirred for 30 min and a suspension of 7-Fluoro-quinoline-6-carbaldehyde (10 g, 57.1 mmol) in 40 ml of THF was added. The resulting mixture was stirred at roomtemperature for 3 hrs and quenched with 400 ml of water. After stirring for additional 1 hr, the precipitate was collected by filtration, washed with EtOAc and dried over vacuum oven overnight to afford 13 g (yield: 69%) of title compound. 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.91 (dd, 1 H), 8.49 (d, 1 H), 8.28 (d, 1 H), 8.24 (d, 1 H), 7.74 (d, 1 H), 7.54(q, 1 H), 7.51 (s, 1 H), 7.40 (d, 1 H), 6.54 (m, 2H).

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
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823-57-4, name is 2-Bromo-5-chloroaniline, 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: C6H5BrClN

Step 2: Preparation of Compound a26 (0680) (0681) To a solution of Compound a25 (1 g, 4.84 mmol) in pyridine (8 mL) was added sodium hydride (0.21 g, 5.33 mmol) and acetyl chloride (0.42 ml, 5.81 mmol), and the solution was stirred at 80° C. for 1 hour. To the reaction solution was added water, and the solution was extracted with ethyl acetate twice. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To a solution of the obtained residue in THF/methanol (1:1, 9 ml) was added 2 mol/L sodium hydroxide aqueous solution (2.6 ml, 5.16 mmol), and the solution was stirred at room temperature for 30 minutes. To the reaction solution was added water, and the solution was extracted with ethyl acetate twice. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained residue was added ethyl acetate (5 ml), and the mixture was dissolved in a water bath of 80° C. After cooled to room temperature, hexane (5 ml) was added to the solution, and the precipitated solid was filtered, washed with isopropyl ether (5 ml), and dried under reduced pressure to Compound a26 (674.4 mg, yield: 53percent) as a pale brown solid. (0682) 1H-NMR (CDCl3) delta: 8.46 (s, 1H), 7.59 (s, 1H), 7.45 (d, 1H, J=8.5 Hz), 6.97 (d, 1H, J=8.5 Hz), 2.25 (s, 3H).

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Tokyo; TOHOKU UNIVERSITY; Shionogi & Co., Ltd.; NAGANO, Tetsuo; OKABE, Takayoshi; KOJIMA, Hirotatsu; KAWAGUCHI, Mitsuyasu; NUREKI, Osamu; ISHITANI, Ryuichiro; NISHIMASU, Hiroshi; AOKI, Junken; TANAKA, Nobuyuki; KANDA, Yasuhiko; KIOI, Yoshiyuki; TATENO, Yusuke; KIDA, Shiro; YAMANE, Junji; (163 pag.)US2017/158704; (2017); A1;,
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Related Products of 6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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.

A mixture of 6-chloroimidazo[1,2-b]pyridazine (3) 19 (768 mg, 5.0 mmol), 4-aminophenol (818 mg, 7.5 mmol), and K2CO3 (2073 mg, 15.0 mmol) in NMP (5 mL) was stirred at 120 C for 18 h. The mixture was diluted with 1 N aqueous NaOH and extracted with EtOAc. The organic layer was washed with 1 N aqueous NaOH and brine and concentrated in vacuo. The residue was purified by basic silica gel column chromatography (hexane/EtOAc 70:30 to 0:100) and triturated with diisopropyl ether to give 4a (759 mg, 67%) as a gray solid. 1H NMR (DMSO-d6) delta 5.07 (2H, s), 6.60 (2H, d, J = 8.9 Hz), 6.92 (2H, d, J = 8.9 Hz), 7.00 (1H, d, J = 9.8 Hz), 7.61 (1H, s), 8.01 (1H, s), 8.09 (1H, d, J = 9.8 Hz).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Miyamoto, Naoki; Oguro, Yuya; Takagi, Terufumi; Iwata, Hidehisa; Miki, Hiroshi; Hori, Akira; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7051 – 7058;,
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Related Products of 38762-41-3,Some common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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.

A. Tert-butyl N-(4-bromo-2-chlorophenyl)carbamate A solution of 4-bromo-2-chloroaniline (5.00 g, 0.0242 mol) in tetrahydrofuran (50 mL) was reacted with a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (53.2 mL, 0.0532 mol). The mixture was stirred 15 minutes at ambient temperature. Di-tert-butyl dicarbonate (6.34 g, 0.0290 mol) was added and the solution was stirred for 2 hours. The solvent was removed in vacuo, and the crude material was purified by flash column chromatography on silica using heptane /ethyl acetate (4:1). The solvent was removed in vacuo to give tert-butyl N-(4-bromo-2-chlorophenyl)carbamate as a white solid (4.214 g, 0.0137 mol). 1H NMR (DMSO-d6, 400 MHz) delta 8.75 (s, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 7.50 (dd, 1H), 1.46 (s, 9H); TLC (heptane/ethylacetate 4:1) Rf 0.54.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-chloroaniline, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
Chloride – Wikipedia,
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2106-02-7, name is 2-Chloro-4-fluoroaniline, 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. Computed Properties of C6H5ClFN

Production of ethyl (3S)-3-{[(2-chloro-4-fluorophenyl)amino]sulfanyl}-3,6-dihydro-2H-pyran-4-carboxylate To a solution (400 mL) of ethyl (3S)-3-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylate (14.5 g) in dichloromethane was added dropwise tert-butyl hypochlorite (10 mL) at -78C. After stirring for 30 min, 2-chloro-4-fluoroaniline (23 mL) was added dropwise at -78C. The reaction mixture was stirred for 1 hr, and the reaction was discontinued with 5% aqueous sodium sulfite solution (300 mL). After extraction with dichloromethane (300 mL), the extract was washed with water, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=15:1?5:1) to give the title compound as a crude product (20.0 g, 96.3 %ee). This product was crystallized from diisopropyl ether/hexane (120 mL, 1:5) to give the title compound (12.3 g, 62%) as white crystals. 1H-NMR (CDCl3) delta: 1.33 (3H, t, J = 7.2 Hz), 3.72-3.79 (2H, m), 4.20-4.46 (5H, m), 5.53 (1H, br s), 6.90-7.03 (3H, m), 7.54-7.59 (1H, m). enantiomeric excess: >99 %ee [column: CHIRALPAK AD (manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.), mobile phase: hexane/2-propanol = 97.5/2.5].

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KITAMOTO, Naomi; (26 pag.)EP2528598; (2016); B1;,
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