Month: March 2021

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

Will 25g compound 214.5g of compound 3,400 mL of isopropanol was added to the reaction flask.Warming up to reflux for 3 h,After the TLC detection reaction is completed, the temperature is lowered to 0 to 40 C, and suction filtration is performed.Then drying at 40 to 50 C to obtain 35 g of compound 4;

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tonghua Normal College; Geng Xiaoyu; Xue Mingxing; Zang Hao; Liu Xuekun; Sun Renshuang; Xue Changsong; Zhang Haifeng; (13 pag.)CN109438423; (2019); A;,
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Related Products of 1435-48-9, 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 1435-48-9 as follows.

(S)-3-((R)-1-Hydroxy-2-methoxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (10.0 mg, 40.8 mumol) was dissolved in DMF (0.1 mL). NaH (1.5 mg, 61.1 mumol) was slowly added and the mixture was stirred at room temperature for 15 minutes. Then, 2,4-dichloro-1-fluorobenzene (20.2 mg, 122 mumol) was added. The mixture was stirred at 100 C. for 1 hour, then cooled to room temperature. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) and stirred overnight at room temperature. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (12.8 mg, 99% purity). MS m/z: [M+H]2+ calcd for C13H17Cl2NO2, 290.06; found 290.0.

According to the analysis of related databases, 1435-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STANGELAND, Eric; SCHMIDT, Jane; SAITO, Daisuke Roland; HUGHES, Adam; PATTERSON, Lori Jean; US2011/21597; (2011); A1;,
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Synthetic Route of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: Following the similar procedures as for compound 13a gave compound13b, white solid, 55percent. 1H NMR (400 MHz, CDCl3) delta 8.10 (d,J=5.1 Hz, 1H), 7.43 (d, J=1.8 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H),7.21?7.15 (m, 1H), 6.84 (d, J=5.1 Hz, 1H), 4.79 (t, J=5.6 Hz, 1H),4.65?4.59 (m, 2H), 3.78?3.68 (m, 1H), 3.62?3.53 (m, 2H), 3.21 (t,J=6.3 Hz, 2H), 3.05?2.95 (m, 2H), 2.82 (s, 3H), 2.78 (s, 3H), 2.58 (t,J=6.9 Hz, 2H), 2.43?2.33 (m, 2H), 2.08?1.98 (m, 4H), 1.87?1.76 (m,4H), 1.72?1.61 (m, 2H). 13C NMR (126 MHz, CDCl3) delta 169.41, 154.57,146.52, 144.37, 140.39, 132.47, 130.98, 130.44, 129.56, 127.05,114.53, 112.28, 55.59, 54.97, 53.01, 46.27, 45.72, 44.85, 38.50, 29.69,28.71, 28.56, 26.62, 22.37. HRMS (ESI): calcd for C26H36Cl2N5O3S [M+H]+: 568.1910; found 568.1898. Retention time 2.35 min,>97percentpure.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Li-Huai; Wang, Zhi-Long; Xie, Xin; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3559 – 3572;,
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Electric Literature of 821-10-3, These common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, 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 diyne (50 mg) in dry solvent (5mL) in microwave reaction vessel propargyl halide 7b/c/e/f (2 equiv.) and Mo(CO)6 (5 mol%) were added andthe reaction mixture was irradiated in a CEM Discover microwave synthesizer for10 min. under standard conditions. Afterthe completion of reaction (TLC monitoring), the solvent was concentrated atreduced pressure and the crude product was purified by silica gel columnchromatography

The synthetic route of 821-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kotha, Sambasivarao; Sreevani, Gaddamedi; Tetrahedron Letters; vol. 56; 43; (2015); p. 5903 – 5908;,
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Electric Literature of 202925-07-3, 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. 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

2- Chloro-3-fluoro-6-methoxybenzaldehydeTo a solution of 2-chloro-1 -fluoro-4-methoxybenzene (28.5 g, 178 mmol) in i-butyl methyl ether (200 mL, dried over anhydrous MgS04) at -78 C was added 2.5 M n-butyl lithium in hexanes (107 mL, 268 mmol). After 3 h, methyl formate (18.76 mL) was added dropwise while keeping the temperature below -60 C. The reaction mixture was quenched with sat. aq. ammonium chloride (250 mL) after 45 minutes and the organic layer was separated. The aq. layer was extracted with ethyl acetate (2×100 mL), and the combined organic layers were washed with water (200 mL) followed by brine, dried (Na2S04) and concentrated to give a residue which on trituration with hexanes gave solids. The solids were filtered, taken again in hexanes and heated over a steam bath. The mixture was cooled, and the light yellow desired product filtered off and air-dried to give the title compound. 1H NMR (400 MHz, CDCI3): delta = 10.48 (d, J = 0.8 Hz, 1 H), 7.31 (dd, J = 9.4, 7.8 Hz, 1 H), 6.88 (dd, J = 7.8, 3.8 Hz, 1 H), 3.92 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1-fluoro-4-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; LI, An-Hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WO2011/143646; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1298031-93-2, 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. 1298031-93-2, name is 6,8-Dichloro-2-methylimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of intermediate 2 (250 g), morpholine ([CAS 110-91-8], 103 g, 1190 mmol)and N,N-diisopropylethylamine ([CAS 7087-68-5], 208.7 g, 1623 mmol) in CH3CN (2000 mL) was refluxed for 5 h. Then, the reaction mixture was concentrated underreduced pressure and the residue was purified by column chromatography over silicagel (eluent: petroleum ether/ethyl acetate, 3/1) to give 70 g (22.4%) of intermediate 3 as a yellow solid.

The synthetic route of 6,8-Dichloro-2-methylimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LECLERCQ, Laurent, Christian, L.; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; VAN GOOL, Michiel, Luc, Maria; WO2014/9305; (2014); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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: 6-Chloroimidazo[1,2-b]pyridazine

General procedure: [0129] To a suspension of Zn powder (2.5 g, 38 mmol) in 1,4-dioxane (40 ml) was added iodine (0.9 mmol) and themixture was placed under an atmosphere of nitrogen. The benzyl bromide (19 mmol) was added in portions (after thefirst portion the mixture was gently heated to initiate reaction). Subsequent portions did not require heating and once allthe portions were added the mixture was allowed to stir at room temperature for 4 hours. After this time the mixture wasallowed to settle and the liquid was decanted from the excess Zinc and the resulting solution could be used immediatelyin the next reaction.[0130] A solution of the alkyl Zinc reagent (see note below) (2 eq.) was added to NiCl2dppp (10 mol %) under anatmosphere of nitrogen and the mixture was stirred at room temperature for 5 minutes. After this time the 6-chloroimidazo[1,2-b]pyridazine (1 eq.) was added as a solid in one portion and the mixture was heated at 50 C for 18 hours.The mixture was cooled to room temperature and a saturated aqueous solution of NH4Cl was added followed by EtOAc.The mixture was filtered through celite and the phases were separated. The organic phase was washed with brine, dried(MgSO4) and concentrated under reduced pressure and the residue was purified by column chromatography on silicagel (mixtures of Ethyl Acetate and Petroleum Ether

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6775-78-6, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Chloride – Wikipedia,
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Application of 108-37-2,Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, 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 thermal characteristics of this reaction were studied using an HEL Simular reaction calorimeter. The calorimeter was equipped with a double-jacketed, 0.8-liter, glass reactor (6 bars). The inner jacket contained a heat-transfer fluid and the outer jacket was evacuated to insulate the system. A quantity of 26.5 g (0.139 moles, 1 equivalent) of 3-bromochlorobenzene (10), 200 ml of 2-methyltetrahydrofuran (Me-THF) and 15.0 g (0.158 moles, 1.1 equivalents) of anhydrous magnesium chloride was charged to this reactor. The slurry was then cooled to -78 C. A quantity of 91.2 ml (0.158 moles, 1.3 equivalents) of lithium diisopropylamide (LDA, 2M in heptane/THF) was charged into the batch, keeping the temp ?75 C. The batch was held for an hour after LDA addition. A quantity of 15.0 ml (0.194 moles, 1.4 equivalents) of N,N-dimethylformamide was charged into the batch at -78 C., keeping the temperature ?75 C. The mixture was stirred for an hour and gradually warmed to 0 C. At 0 C., the reaction was quenched with 150 ml of 0.5M citric acid solution. The layers were separated and the organic layer was collected and concentrated to dryness. The desired product (12) was isolated in 80% yield and 99% purity by GC.

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-3-chlorobenzene, its application will become more common.

Reference:
Patent; Ji, Yaohui; Rawalpally, Thimma; US2009/118546; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2687-12-9, 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. 2687-12-9, name is Cinnamyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 25 mL high pressure dad, Palladium acetylacetonate (15.2 mg, 0.05 mmol) was added, Tetrabutylammonium chloride (277.9 mg, 1.0 mmol), Potassium fluoride (58.lmg, 1.0 [eta] [eta] & lt; 1 & gt;), And a stirring magnet was charged. After nitrogen substitution three times, Add cinnamyl chloride to high pressure dad (152.6 mg, 1.0 mmol,), Tetrahydrofuran (2 mL), Boronic acid pinacol ester (168. Omg, 1.O mmol), The charging port and the charging port are then closed. Carbon dioxide high pressure cylinders are connected to one atmosphere of carbon dioxide gas. The autoclave was stirred in a 90 C oil bath for 24 hours. After completion of the reaction, Slowly release the excess carbon dioxide, The reaction solution was transferred onto a 30 cm high silica gel column, Using petroleum ether: ethyl acetate as a developing solvent of 100: 1 column, The pure product was isolated, The yield of this reaction was 95%.

The synthetic route of Cinnamyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Feng, XiuJuan; Sun, Jian; Bao, Ming; Yu, Xiaojiang; Zhang, Sheng; (25 pag.)CN105777463; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 5527-94-6, 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. 5527-94-6, name is 4-Chloro-3-fluorotoluene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Step 1) Synthesis of 1-chloro-2-fluoro-4-methyl-5-nitrobenzene 1-Chloro-2-fluoro-4-methylbenzene (1.00 g) was dissolved in TFA (10 mL). The solution was cooled to 0 C., and then, fuming nitric acid (5.0 mL) was added dropwise thereto. The mixture was stirred at 0 C. for 30 minutes, and then, the solution was added to an aqueous sodium bicarbonate solution and neutralized, followed by extraction with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to obtain 1.31 g of the title compound as a white solid.

The synthetic route of 4-Chloro-3-fluorotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; KAWAI, Yuichi; IRIE, Hiroki; SAGARA, Takeshi; MIYADERA, Kazutaka; (63 pag.)US2017/217970; (2017); A1;,
Chloride – Wikipedia,
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