Category: chlorides-buliding-blocks

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. 7006-52-2, name is N-Methyl-3-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

General procedure: Bi(NO3)3.5H2O (2 equiv, 0.6 mmol), Pd(OAc)2 (0.015 mmol, 5 mol percent) were added into a 25mL oven-dried Schlenk tube, the tube was evacuated and backfilled with Ar (repeated three times in 30 min). Under a counter flow of Ar, N-substituted aniline (1 equiv, 0.3 mmol) was added by syringe firstly, 1.5 mL TFE and 0.5 mL TFA were then added by disposable medical syringes. The flask was sealed and the mixture was stirred firstly at room temperature for15 min, then allowed to stir in a preheated oil bath at 90 °C for 24 h.The mixture was cooled to room temperature when the reaction was completed. Next, the solution was diluted by 10 mL ethyl acetate and filtered the insoluble matters, washed the organic phases by 5percent NaHCO3 solution after the extraction, and extracted the aqueous phases by ethyl acetate (3×15 mL) to collect organic phases. All the organic solutions were washed by brine, dried 30 min with anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude products were purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether(5/1-2/1).

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Yi-Si; Mao, Long; Bu, Xiao-Song; Dai, Jian-Jun; Xu, Hua-Jian; Tetrahedron; vol. 71; 23; (2015); p. 3827 – 3832;,
Chloride – Wikipedia,
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Electric Literature of 13918-92-8, A common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

Reference Example 143; tert-butyl ({5- (2-cyanopyridin-3-yl) -l-[ (2,4- difluorophenyl) sulfonyl] -lH-pyrrol-3-yl}methyl)methylcarbamate; To a suspension of sodium hydride (60% in oil, 26.0 mg) in tetrahydrofuran (3 mL) was added tert-butyl {[5- (2- cyanopyridin-3-yl) -lH-pyrrol-3-yl]methyl Jmethylcarbamate (156 mg) at room temperature, and the mixture was stirred for 15 min. After stirring, 15-crown-5 (143 mg) and 2,4- difluorobenzenesulfonyl chloride (159 mg) were added dropwise and the mixture was further stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9: 1-*2: 1) to give the title compound as a colorless oil (yield 208 mg, 85%).1H-NMR (CDCl3) delta: 1.48(9H,s), 2.85 (3H,brs) , 4.29 (2H,brs) , 6.46(lH,brs) , 6.80-6.88 (IH,m) , 6.93 (lH,ddd, J=IO.2, 8.1, 2.4Hz) , 7.20(lH,ddd, J=8.8, 8.0, 5.8Hz) , 7.46 (IH, s) , 7.55(lH,dd, J=7.9,4.7Hz) , 7.93 (IH, dd, J=8.0, 1.6Hz) , 8.69(lH,dd, J=4.7,1.7Hz) .

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 468075-00-5,Some common heterocyclic compound, 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, molecular formula is C7H3BrClF3O, 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 2-bromo-l-chloro-4-(trifluoromethoxy)benzene (5.00 g, 18.15 mmol), Pd(dppf)Cl2.CH2Cl2 (1.48 g, 1.82 mmol) and Et3N (5.51 g, 54.45 mmol) in EtOH (30 mL) was degassed, and refilled with CO. The reaction was stirred under CO (50 psi) for 16 hours at 80 C, at which point the desired product was observed by LCMS. The reaction mixture was diluted with EtOH (20 mL), and filtered through a Celite pad. The filtrate was concentrated. The residue was purified by flash chromatography on silica gel (EtOAc in PE = 0% 5%) to afford compound 12-b (2.40 g, 8.93 mmol) as an oil. 1H NMR (400MHz, CDC13) deltaH = 7.66 – 7.59 (m, 1H), 7.42 (d, 1H), 7.24 – 7.19 (m, 1H), 4.36 (q, 2H), 1.35 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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Electric Literature of 108649-59-8, 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. 108649-59-8 name is 1-(2-Bromoethyl)-2,4-dichlorobenzene, 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.

General procedure: Magnesium turnings (13.2 g, 0.55 mol) were placed in dry THF (25 mL) undernitrogen. A small amount (10 mL) of (2-bromoethyl)benzene (92.5 g, 0.50 mol) dissolvedin dry THF (300 mL), added to the magnesium slurry and stirred for a few minutes withwarming until the reaction commenced. The remainder of the (2-bromoethyl)benzenesolution was added dropwise to maintain reflux over an hour, then the reaction mixturewas aged at reflux for an additional an hour. The reaction mixture was cooled to 25 C. In a separate flask, diethyl oxalate (88.2 g, 0.6 mol) was dissolved in dry THF (100mL) and cooled to -10 C. The supernatant solution of (2-phenylethyl)magnesiumbromide was sucked under nitrogen through a sintered-glass filter into a dropping funnel.The reaction temperature was held at -10 C as the solution of Grignard reagent wasadded dropwise over an hour to the diethyl oxalate. The sintered-glass funnel anddropping funnel were then rinsed with dry THF (100 mL), and the rinse was added to thebatch. The reaction mixture was allowed to stand for 30 min and then quenched byaddition of 3 M HCl (145 mL).Hexane (500 mL) was added, and the aqueous layer was discarded. The organicphase was washed with brine (100 mL) and saturated NaHCO3 (100 mL), until theaqueous layer measured to pH 5.0. The organic phase was dried with anhydrous Na2SO4.Filtered and washed with hexane, and the combined layers were concentrated to an oil invacuum. The crude keto ester (103.0 g) was vacuum distilled at 105-110 C (0.2-0.3 mmHg) to afford a colourless oil 90.0 g with 60% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethyl)-2,4-dichlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Lufeng; Chen, Houhe; Meng, Qinghua; Fan, Weizheng; Xie, Xiaomin; Zhang, Zhaoguo; Tetrahedron; vol. 67; 34; (2011); p. 6186 – 6190;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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 13078-79-0, Quality Control of 2-(3-Chlorophenyl)ethanamine

General procedure: 2.5mmol Thiazole-4-carboxyli acid and 2.0mmol amine were dissolved in 25mL DCM in a dry flask with continuous stirring, followed by the addition of 2.5mmol 3-(3-Dimethylaminopropyl)-1-Ethylcarbodiimide Hydrochloride (2.5mmol). When the temperature of the reaction system cooled to 0C, 50mg 4-dimethylaminopyridine (0.2mmol) was added dropwise and reacted for 1hat 0C. Then the reaction temperature was elevated to room temperature for another 4h. The reaction was stopped by adding 25mL saturated NaHCO3 solution and extracted twice with 20mL dichloromethane (2×20mL). The extracted organic layers were first dried by anhydrous Na2SO4, and then filtered and concentrated under vacuum distillation, obtaining the crude products. Finally, the crude products were further purified using column chromatography (ethy lacetate: petroleum ether, 1:5).

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:
Article; Li, Shengrong; Chen, Siyu; Fan, Jilin; Cao, Zhen; Ouyang, Weihao; Tong, Ning; Hu, Xin; Hu, Jie; Li, Peishan; Feng, Zifeng; Huang, Xi; Li, Yuying; Xie, Mingshan; He, Ruikun; Jian, Jingyi; Wu, Biyuan; Xu, Chen; Wu, Weijian; Guo, Jialiang; Lin, Jing; Sun, Pinghua; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 64 – 73;,
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Application of 19752-55-7, 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A 250 ml round-bottom flask was argonated and consecutively charged with Et2O (60 ml), Mg (1.31 g; 54.0 mmol), I2(one crystal), and a solution of 1-bromo-3,5-dichlorobenzene (12.54 g; 55.5 mmol) in Et2O (60 ml) was added in ca. 5 ml portions over 45 min. Stirring was continued for 3 h at RT, and a solution of 9c (9.52 g; 18.0 mmol) in hot toluene (60 ml, ca. 90 °C) was added slowly, and the mixture was heated to 40 °C for 15 h. A precipitate was decanted, washed with toluene (2 30 ml), treated with concd HClaq. (100 ml) at reflux for 3 h, and cooled to RT. The resulted precipitate was filtered, washedwith concd HClaq. (2 30 ml), and dried. Then, most of the beige solid was dissolved in a hot mixture of water (40 ml), concd HClaq. (120 ml) and ethanol (30 ml), resulted solution was decanted, cooled to RT, and part of the solvent (ca. 50 ml) wasslowly evaporated under reduced pressure. The resulted suspension was filtered, and collected filtrate was washed with concdHClaq. (2 30 ml), and dissolved in CH2Cl2 (150 ml). The organic phase was washed with brine (100 ml), and dried overMgSO4. Then, the mixture was filtered, n-heptane (40 ml) was added, and the mixture was slowly evaporated at 300 mbar (very slow rotations, no heating bath applied). The resulted precipitate was filtered, washed with n-hexane, and dried in vacuo. Filtrate was evaporated and the crystallization procedure was repeated. Both crops were collected and combined to obtain 10c (6.70 g; 9.07 mmol; 50percent calculated as a bromide) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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 61881-19-4, Product Details of 61881-19-4

To a solution of 28 (0.91 g, 1.7 mmol) in acetone (17 mL) wereadded CF3C(=NPh)Cl (0.53 mL, 3.3 mmol) and K2CO3 (1.1 g,8.3 mmol) at 0 C. After stirring for 2.5 h at the same temperature, thecompletion of the reaction was confirmed by TLC (5:1 n-hexane/EtOAc). The reaction mixture was filtered through Celite pad and thepad was washed with CHCl3. The filtrate and washings were concentrated.The resulting residue was purified by silica gel columnchromatography (25:1 n-hexane/EtOAc) to give 29 (1.2 g, quant.) ascolorless syrup. 1H NMR (500 MHz, CDCl3) delta 7.44-6.70 (m, 17H, Ar),5.08-4.83 (br m, 4H, H-1, H-2, H-3, H-4), 4.15-3.65 (br m, 3H, H-5, H-6a, H-6b), 1.08 (s, 9H, tBu), 1.01 (s, 9H, tBu); 13C NMR (125 MHz,CDCl3) delta 143.5, 143.3, 138.9, 138.6, 135.4, 135.3, 135.3, 135.2, 133.1,133.1, 128.7, 128.4, 128.4, 128.3, 128.2, 128.2, 128.1, 128.1, 128.0,127.9, 127.7, 127.7, 127.7, 126.9, 126.5, 126.2, 126.1, 126.1, 126.0,126.0, 125.6, 124.4, 119.4, 119.2, 84.0, 81.2, 80.0, 77.9, 77.7, 77.5,75.8, 75.5, 75.5, 73.9, 71.0, 68.8, 66.5, 66.2, 27.4, 27.0, 26.9, 22.7,20.0. HRMS (ESI) m/z: found [M+Na]+ 744.2935, C40H46F3NO6Sicalcd for [M+Na]+ 744.2939.

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:
Article; Takato, Koichi; Kurita, Motoki; Yagami, Nahoko; Tanaka, Hide-Nori; Ando, Hiromune; Imamura, Akihiro; Ishida, Hideharu; Carbohydrate Research; vol. 483; (2019);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 823-57-4, A common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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 corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous bromide (0.02 mmol), 2-bromo-5-chloroaniline (0.4 mmol),1,10-azaphenanthroline (0.04 mmol), potassium carbonate (0.6 mmol),Carbon disulfide (0.6 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 110 C oil bath and stirred for 12 hours.The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction solution.Mix well, each time with 3mL of ethyl acetate as extractant through liquid separation extraction operation,The crude product is extracted from the reaction solution, and the extract is combined.The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (silica gel, 200 to 300 mesh, eluent, petroleum ether/ethyl acetate (10:1 v/v)).The target product was obtained in 65.2 mg, yield 83%.

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

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Chloride – Wikipedia,
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Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

In the reaction (r-1 ‘), a benzene derivative (3A’) (15.2 g, 0.1 mol) and triethyl phosphite represented by the chemical formula (B) (25 g, 0.15 mol ), And the mixture was stirred at 180 C. for 8 hours and then cooled to room temperature. Thereafter, unreacted or remaining triethyl phosphite was distilled off under reduced pressure to obtain a phosphonate derivative (3C ‘) as a white liquid. The yield from the benzene derivative (3A ‘) of the phosphonate derivative (3C’) was 23.5 g (yield: 92 mol%).

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyocera Document Solutions Co., Ltd.; Okada, Hideki; Sugai, Akio; Kojima, Kensuke; (52 pag.)JP2017/114808; (2017); A;,
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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrClO

EXAMPLE 21 Preparation of 5-Hydroxy-3-(3-chloro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one of Formula (67) [0134] A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3*35 ml), washed with water (2*20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A) [0135] wherein R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (1.32 g, 37%). [0136] A solution of the above alcohol of the formula (4A) wherein R1=R5=R6 =R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl wherein (0.95 g, 1.83 mmol) in dry dichloromethane (15 ml) was cooled to 0 C., pyridinium dichromate (1.92 g, 8.17 mmol) was added and the mixture was stirred at room temperature for 3 h. Filtration through celite (3.00 g), washing with dichloromethane (30 ml) and concentration afforded the crude product which was purified by silica gel column chromatography (eluent-3% acetone in pet ether) to yield the title compound of the formula (1B) wherein R=OTBS, R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (0.32 g, 34%), which on deprotection of TBDMS group using the procedure described in example 10 furnished the compound of formula (67). [0137] Spectral data of compound of the formula of structure (67) [0138] 1H NMR(CDCl3+CCl4): delta 2.96 (dd, J=18 Hz and 2 Hz, 1H), 3.33 (dd, J =18 Hz and 6 Hz, 1H), 3.75 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45-4.54 (m, 1H), 6.42 (s, 2H), 6.81 (d, J=8 Hz, 1H), 7.21-7.29 (m, 1H), 7.48 (bs, 1H). [0139] 13C-NMR (CDCl3+CCl4): delta 37.79, 55.87 (2C), 60.58, 71.57, 106.23 (2c), 111.31, 122.41, 126.82, 127.59, 128.58 (2C), 130.05, 135.90, 138.07, 153.36 (2C), 156.48, 162, 51, 206.95

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; DABUR RESEARCH FOUNDATION; US2003/229146; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics