Tag: M.W=200-300

Some common heterocyclic compound, 4263-52-9, name is Sodium 2-bromoethanesulphonate, molecular formula is C2H4BrNaO3S, 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. 4263-52-9

10.5 g sodium 2-bromoethanesulfonate was added to a solution of 110 ml benzyl alcohol and 1.15 g sodium benzyloxide.Then the mixture was boiled under reflux four times. The mixture was then concentrated under vacuum to dryness and then boiled with ethyl alcohol three times. The alcohol was filtered and concentrated to dryness.The yield was 9.8 g and was confirmed by UV and IR.Pure crystals were obtained by boiling the resultant sodium 2-benzylether ethanesulfonate in ethyl alcohol, filtering, then cooling the solution to crystallize pure sodium 2-benzylether ethanesulfonate crystals out of solution.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4263-52-9, its application will become more common.

Reference:
Patent; GEISTLICH PHARMA AG; PFIRRMANN, Rolf W.; (101 pag.)WO2016/98054; (2016); A1;,
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A common heterocyclic compound, 444-14-4, name is 2-Bromo-4,6-difluoroaniline, molecular formula is C6H4BrF2N, 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. 444-14-4.

3. Amination The 1-bromo-3,5-difluorobenzene generated by diazotization of 2-bromo-4,6-difluoroaniline can be converted to 100 lbs. of 3,5-difluoroaniline as follows: A suitable pressure reactor designed for a minimum of 300 psig pressure is charged with 288.1 lbs. of 29% aqueous ammonia. The reactor is designed to provide for pressure control via temperature control of the reaction. To the ammonia charge, 4.7 lbs. of cuprous oxide is added, and the 168.2 lbs. of crude 1-bromo-3,5-difluorobenzene product is added. The reaction mixture is heated to about 135 C. using temperature control to maintain a maximum pressure of 300 psig, and the reaction pressure is maintained at about 300 psig by slowly increasing the reaction temperature to 165 C. over 4.5 hours. The reaction mixture is held at 165 C. for one additional hour, and then a sample is assayed for completeness of the reaction. If more than 0.5% by weight of 1-bromo-3,5-difluorobenzene remains unreacted, then the reaction mixture is held at 165 C. for one more hour and re-assayed. This process is repeated until less than 0.5% by weight of unreacted 1-bromo-3,5-difluorobenzene remains.

The synthetic route of 2-Bromo-4,6-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Corporation; US5977412; (1999); A;,
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22385-77-9, Adding some certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 22385-77-9.

General procedure: To a solution of phthalimide (20 mmol) in CH2Cl2 (70 mL) was added the Grignard reagent (preformed from 50 mmol ArBr, 60 mmol mg in 30 mL THF) at room temperature. The resulting mixture was stirred at room temperature for 1.5 h and quenched with saturated aqueous solution of NH4Cl (40 mL). Then the mixture was extracted with ethyl acetate and washed with brine. The collected organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography, eluting with ethyl acetate/petroleum ether 1:1 (v/v), to afford the 3-aryl-3-hydroxyisoindolin-1-ones.

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 22385-77-9.

Reference:
Article; Ge, Chen; Liang, Ren-Xiao; Liu, Ren-Rong; Xiang, Bin; Jia, Yi-Xia; Tetrahedron Letters; vol. 58; 2; (2017); p. 142 – 144;,
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626-40-4, 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. 626-40-4, name is 3,5-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

Compound II (2.25 g, 10 mmol),Compound III (2.51 g, 10 mmol) andDiisopropylethylamine (DIPEA, 3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene,Then heated to reflux under nitrogen,Until the reaction is complete (usually 5 hours).The reaction mixture was carefully poured into 200 mL of ice water,Stirred, extracted with 50 mL x 3 CH2Cl2,Combined extraction phase,Washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL), and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration and the filtrate was evaporated to dryness on a rotary evaporator to give compound IV, a white solid,

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Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN106749368; (2017); A;,
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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 2606-51-1 as follows. 2606-51-1

General procedure: Benzyl bromide (1 g) in dry toluene (15 mL). To this tripheylphosphine (1.5 g) was added and the reaction mixture was refluxed for 1-3 h at 120 C to get the wittig salt as precipitate. It was filtered and washed with dry benzene (yield 62-87%).

According to the analysis of related databases, 2606-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parihar, Swati; Kumar, Amit; Chaturvedi, Amit K.; Sachan, Naresh Kumar; Luqman, Suaib; Changkija, Bendangla; Manohar, Murli; Prakash, Om; Chanda; Khan, Feroz; Chanotiya; Shanker, Karuna; Dwivedi, Anila; Konwar, Rituraj; Negi, Arvind S.; Journal of Steroid Biochemistry and Molecular Biology; vol. 137; (2013); p. 332 – 344;,
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327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Dissolve 2,4,5-trifluorobromobenzene (10.5 g 49.8 mmol) in tetrahydrofuran (25 mL) with methyl tert-butyl ether(25 mL), cooled to -30 C, isopropyl magnesium chloride (4.8 g 46.5 mmol) was slowly added dropwise to the solution, stirred at -30 C for 10 min, and added with cuprous chloride (1.6 g 16.6 mmol). After stirring at -30C for 15 min, the compound of formula 3 (6.1 g 33.2 mmol) was dissolved in methyl tert-butyl ether (20 mL) and slowly added dropwise to the reaction system. The temperature rose from -30C to -3C within 3 h. At 10C, it was warmed to -5C over a further 3 h and reacted overnight at 0C. Saturated ammonium chloride (25 mL) was added to the reaction system, extracted with ethyl acetate (20 mL*1), washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and stirred with petroleum ether (50 mL) to obtain 15.6 g. Product 4, yield 90%.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heding (Nanjing) Pharmaceutical Co., Ltd.; Li Wensen; (18 pag.)CN105017081; (2017); B;,
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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 1435-51-4 as follows. 1435-51-4

Example 23-Difluoromethyl-5-(2,3-difluoro-6-nitrophenoxy)benzonitrile (FIGURE 2;ROUTE B).step 7; – /?-Methoxybenzyl alcohol (12.4 kg, 89.8 mol) was added slowly to a mixture of potassium tert-butoxide (10.0 kg, 89.4 mol) in THF (78 L) allowing the reaction exotherm to raise the temperature to ca. 35 C. After stirring at 35 to 40 C for 0.5 h, 25 (21.4 kg, 84.3 mol) was added slowly allowing the reaction to exotherm to reach ca. 60 0C. After stirring at 60 C for 2 h the reaction was monitored by hplc. After cooling to RT, HOAc (ca. 600 g) and then water (30 L) was added and the phases separated. The aqueous phase was extracted with EtOAc (20 L) and the combined organic phases washed with a mixture of saturated brine (10 kg) and water (10 L). The organic phase was concentrated in vacuo (ca. 27 inches Hg, jacket temperature ca. 65 0C) to afford an oil. MeOH (ca. 43 kg) was added to form a biphasic mixture which was aged at 45 to 50 C. The product precipitated and the slurry was stirred until a uniform consistency was achieved. After cooling to RT, and aging overnight, the product was filtered off, washed with MeOH (9.8 kg), and dried under vacuum at 50 C to afford 26.06 kg of 40. The material remaining in the reactor and filter was dissolved in THF (ca. 10 L) and the solution evaporated to dryness on a rotary evaporator to afford an additional 3.44 kg (94% overall)

According to the analysis of related databases, 1435-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/145563; (2008); A2;,
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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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 327-52-6

Step 1: (2-Bromo-4,5-difluorophenyl)(methyl)sulfaneIn a 40 mL vial, a solution of 1-bromo-2,4,5-trifluorobenzene (2.00 g, 9.48 mmol)in DMSO (15 mL) was treated with NaSMe (3.32 g, 47.4 mmol), and the resultingsuspension stirred at room temperature for 4 h. The reaction mixture was diluted with DCM, and the organics were washed with water and brine. The volatiles were concentrated to give (2-bromo-4,5-difluorophenyl)(methyl)sulfane (2.20 g, 98 %), which was used without further purification in next reaction. ?H NMR (400MHz, CDC13) oe7.23 (dd, J=8.7, 5.7 Hz, 1H), 6.98 (dd, J=8.5, 6.4 Hz, 1H), 2.46 (s, 3H). HPLC: RT =2.756 mm; (Chromolith ODS S5 4.6 x 50 mm (4 mm grad) 0-100% B. Flow Rate = 4ml/min. Inj. Vol. = 10 uL. Wavelength = 220. Oven Temp. = 40 C. Solvent A: 10%MeOH – 90% H20 -0.1 % TFA. Solvent B: 90% MeOH – 10 % H20 – 0.1 % TFA).

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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 327-51-5

Into a three-necked flask, to 1,4-dibromo-2,5-difluoro-benzene (5.4g, 20.0mmol), compound 16 (12.8g, 42.0mmol), 2M Na2CO3 aqueous solution (40mL, 80.0mmol), DME (40mL), toluene (40mL), Pd[PPh3]4 (1.2g, 1.0mmol) was added, this mixture was refluxed for 8 hr under Ar atmosphere. After the reaction was cooled to room temperature. The sample was transferred to a separatory funnel, added water (100mL), and extracted with CH2Cl2. After drying with MgSO4, filtered, and concentrated. Purification of a sample was purified by silica gel column chromatography to give a white solid. Yield 8.8g, 70% yield.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Idemitsu Kosan Corporation; Kato, Tomoki; Numata, Masaki; Yoshida, K.; Nishimura, Kazuki; Eiwakuma, Toshihiro; Hosokawa, Chisio; (108 pag.)KR101500796; (2015); B1;,
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The chemical industry reduces the impact on the environment during synthesis 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, I believe this compound will play a more active role in future production and life. 28342-75-8

l,5-Dibromo-2,4-difluorobenzene (1, 1.36 g, 5.00 mmol) was dissolved in dry diethyl ether ( 15 mL) and cooled down to -78C. 2.35 M n-Butyllithium in hexane (2.20 mL, 5.25 mmol) was added drop-wise with stirring . After 15 minutes, dry N,N- dimethylformamide (0.77 mL, 10.0 mmol) was added and the resulting mixture was stirred at for 15 minutes and then allowed to warm to ambient temperature. After one hour, the reaction mixture was quenched with 1.0 M aqueous solution of hydrochloric acid ( 15 mL) . Layers were separated and the organic layer was washed with brine ( 15 mL), dried over anhydrous magnesium sulfate and evaporated . The residue was purified by flash column chromatography (Silicagel 60, 0.063-0.200 mm ; eluent: cyclohexane/ ethyl acetate 20 : 1) 5-bromo-2,4-difluorobenzaldehyde (2) as colorless oil which solidified on storage in freezer. Yield : 780 mg (70%) . JH NM R spectrum (300 MHz, CDCI3, deltaEta) : 10.26 (s, 1 H) ; 8.14 (dd, J =9.6 and 8.0 Hz, 1 H) ; 7.05 (d, J = 8.0 Hz, 1 H) .

The chemical industry reduces the impact on the environment during synthesis 28342-75-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVO NORDISK A/S; KRUSE, Thomas; HANSEN, Mikael, Kofoed; MUeNZEL, Martin, Werner, Borchsenius; TH?GERSEN, Henning; SAUERBERG, Per; RASMUSSEN, Jakob, Ewald; BEHRENS, Carsten; H?EG-JENSEN, Thomas; BAL?ANEK, Vojtech; DROBNAKOVA, Zuzana; DRO?, Ladislav; HAVRANEK, Miroslav; KOTEK, Vladislav; ?TENGL, Milan; ?NAJDR, Ivan; VANOVA, Hana; (202 pag.)WO2019/92125; (2019); A1;,
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