Tag: M.W=200-300

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 38380-85-7 as follows. name: 1-Bromo-4-cyclopropoxybenzene

Step 1 : A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for 2 hours. The solution was quenched with NH4Cl (aq. 1 mL) at – 78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 * 15 mL). The organic layer was dried with anhydrous Na2S04, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 min (method 2), m/z = 162.8 [M + H]+.

According to the analysis of related databases, 38380-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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Related Products of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

To a solution of the product from Part B (23.45 g, 16 mmol) in N,N-dimethylformamide (140 mL) was added potassium carbonate (19.3 g, 140 mmol), bis-(2-bromoethyl)ether (9.1 mL, 70 mmol), and 18-Crown-6 (1 g). The slurry was stirred at 60 C. After 16 hr, the reaction was filtered, and the filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water (3×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The product was recrystallized from methanol to provide 19.79 g (70%) of the desired compound as a white solid. (ESMS m/z=405 [M+H]+.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Freskos, John N.; Fobian, Yvette M.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; DeCrescenzo, Gary A.; Hockerman, Susan L.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Villamil, Clara I.; Wang, Lijuan Jane; US2004/10019; (2004); A1;,
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Related Products of 175278-17-8, These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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.

EXAMPLE 94 2-[(phenylsulfonyl)amino]-4-(trifluoromethoxy)benzoic acid The desired product was prepared by substituting 2-bromo-4-(trifluoromethoxy)aniline for 2-bromo-4-isopropylaniline in Examples 2A-D. MS (ESI(+)) m/e 362 (M+H)+, 379 (M+NH4)+, 384 (M+Na)+; (ESI(-)) m/e 360 (M-H)-; 1H NMR (300 MHz, DMSO-d6) delta 7.76 (m, 1H), 7.73 (m, 1H), 7.68 (m, 1H), 7.51 (m, 3H), 7.39 (d, 1H), 7.20 (m, 1H).

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Comess, Kenneth M.; Erickson, Scott A.; Henkin, Jack; Kalvin, Douglas M.; Kawai, Megumi; Kim, Ki H.; BaMaung, Nwe Y.; Park, Chang Hoon; Sheppard, George S.; Vasudevan, Anil; Wang, Jieyi; Barnes, David M.; Fidanze, Steve D.; Kolaczkowski, Lawrence; Mantei, Robert A.; Park, David C.; Sanders, William J.; Tedrow, Jason S.; Wang, Gary T.; US2004/157836; (2004); 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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 701-07-5

General procedure: A degassed solution containing the aryl bromide (9a, 183 mg, 0.852 mmol), anhydrous LiCl (286 mg, 6.82 mmol), Ph3P (112 mg, 0.426 mmol) and Pd(Ph3P)2Cl2 (71.7 mg,0.102 mmol) in anhydrous diglyme (2 mL, final concentration of 9a ca. 0.15 M) was treated dropwise with allyltri(n-butyl)tin (0.32 mL, 1.02 mmol). The reaction mixture was heated at 130C under an argon atmosphere. A sample taken at 6 h and worked up allowed the isolation of 1-allyl-2-isopropoxybenzene.3IR (film): 605, 734, 864, 995, 1046, 1174, 1287, 1372, 1383, 1489, 1587, 1638, 2931,2978, 3077 cm-1. 1H NMR (300 MHz, CDCl3): d 1.33 (d, J D 6.0 Hz, 6H), 3.37 (d, J D6.7 Hz, 2H), 4.54 (septet, J D 6.0 Hz, 1H), 5.00-5.09 (m, 2H), 5.93-6.03 (m, 1H), 6.83-6.89 (m, 2H), 7.12-7.18 (m, 2H). 13C NMR (75 MHz, CDCl3): d 22.2, 34.6, 69.9, 113.0,115.2, 120.2, 127.1, 129.7, 129.9, 137.2, 155.5. MS (EI, 70 eV): m/z (%) 91 (13), 115(12), 119 (46), 133 (46), 134 (100), 135 (10), 176 [M]C(66), 177 [MC1]C(9). MS found:176.1207; C12H16O requires m/z: 176.1201. When the reaction was heated during 14 h, complete consumption of the starting material took place, as determined by GC analysis. Then, the reaction mixture was allowed to attain ambient temperature and was diluted with 25 mL of hexanes and filtered through a short pad of Florisil and Celite (1:1). The filtrate was washed successively with saturated NaF (4 £ 10 mL), H2O (3 £ 10 mL), brine (15 mL) and H2O2 (10 mL of a0.12% P/V solution), dried over Na2SO4 and evaporated in vacuo. The oily residue was re-dissolved in CH2Cl2 and stirred an additional period of 12 h with 200 mg activated fluorous silica. Filtration and evaporation of volatiles afforded 90 mg (73%) of the expected beta-methylstyrene (3), as a colorless oil.IR (film): 606, 782, 862, 959, 1049, 1176, 1289, 1383, 1484, 1596, 1655, 2876, 2933,3070 cm-1. 1H NMR (300 MHz, CDCl3): d 1.35 (d, J D 5.9, 6H, Me2-CH), 1.90 (dd, J D1.5 and 6.6, 3H, Me-CH=CH-Ar), 4.57 (septet, J D 5.9, 1H, Me2-CH), 6.22 (dq, J D 6.0,13.9 and 15.2, 1H, Me-CH=CH-Ar), 6.72 (dq, J D 1.5 and 15.9, 1H, CH3-CH=CH-Ar),6.85-6.90 (m, 2H, ArH), 7.14 (dt, J D 1.5 and 7.7, 1H, 4-H), 7.41 (dd, J D 1.4 and 7.5,1H, 6-H). 13C NMR (75 MHz, CDCl3): d 18.9 (Me-CH=CH-Ar), 22.2 (Me2-CH-O), 70.8(Me2-CH), 114.3 (6-C), 120.7 (5-C), 125.8 (2-C), 125.9 (CH3-CH=CH-Ar), 126.4 (CH3-CH=CH-Ar), 127.5 (3-C), 128.2 (5-C), 154.6 (1-C). MS (EI, 70 eV): m/z (%) 77 (10), 91(24), 105 (13), 107 (9), 115 (17), 117 (12), 119 (69), 133 (54), 134 (100), 147 (12), 176[M]C(52), 177 [MC1]C(7). MS found m/z D 176.1198; C12H16O (MC) requires m/z D176.1201. The spectral data were in full agreement with those described.2,3,5,8

According to the analysis of related databases, 701-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Simonetti, Sebastian O.; Larghi, Enrique L.; Kaufman, Teodoro S.; Organic Preparations and Procedures International; vol. 47; 3; (2015); p. 227 – 231;,
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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. 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 63057-72-7

4-bromo-3-methoxyphenol 10 (19.8 mmol, 5.80 g) was dissolved infreshly distilled THF (200 mL) in an oven-dried three-neck flask underargon. Temperature was cooled down to -78 oC and the solution wasstirred for 30 minutes before dropwise addition of n-BuLi (1.6N in THF,21.8 mmol, 13.6 mL). Once the addition of n-BuLi was completed, themixture was stirred for another 30 minutes at -78 oC before the dropwise addition of freshlydistilled trimethyl borate (59.4 mmol, 6.75 mL) at this temperature. The reaction mixture wasallowed to warm at room temperature and stirred for 5 h. The temperature was cooled down to-20 oC and HCl 1N was slowly added to reach pH = 2-3. The reaction mixture was allowed towarm at room temperature and extracted three times with EtOAc. The organic layers werecombined, washed with brine, dried with MgSO4 and concentrated in vacuo until precipitationoccurred. An amount of hexanes was then added to maximize precipitation. The solution wasfiltered and the solid was filtered and dried under vacuum. The precipitation/filtration procedurewas repeated twice, yielding a total of 3.72 g (73%) of 4 as a white powder. mp = 184-189 oC.1H-NMR (500 MHz, CDCl3): delta = 4.02 (3H, s), 5.26 (2H, s), 7.01 (1H, d, J = 8.33), 7.31-7.50(5H, m), 7.77 (2H, dd, J = 7.78, 1.28). 13C-NMR (125 MHz, CDCl3): delta =56.05, 70.62, 112.97,117.98, 127.21, 127.96, 128.64, 129.71, 136.81, 149.06, 152.09. 11B-NMR (160 MHz, CDCl3): delta= 27.69. IR (NaCl): numax 1502, 1455, 1398, 1249, 1217, 1183, 1134, 1012, 846, 795, 746,697cm-1. HPLC (Retention time, %): 16.92 min, >99%. HRMS (ESI-TOF, m/z): calcd forC14H14BO3 (M-H2O+H)+ = 241.1033, found 241.1031.

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; Cardinal, Sebastien; Voyer, Normand; Tetrahedron Letters; vol. 54; 38; (2013); p. 5178 – 5180;,
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Related Products of 60876-70-2,Some common heterocyclic compound, 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, molecular formula is C10H13BrO, 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.

Example 2 In a one-liter four-necked flask equipped with a stirrer and a reflux condenser, purged with nitrogen and dried was placed 24.3 g (1.0 mol.) of metallic magnesium flakes to which were added 10 ml of anhydrous diethyl ether and 2 ml of ethyl bromide. After confirming initiation of the reaction by bubbling on the surface of the metallic magnesium, a solution of 114.6 g (0.5 mol.) of p-tert-butoxybromobenzene in 400 ml of anhydrous diethyl ether was added dropwise at the refluxing temperature over approximately 1 hour, and stirring was continued for 5 hours to give p-tert-butoxyphenylmagnesium bromide.

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-4-(tert-butoxy)benzene, its application will become more common.

Reference:
Patent; HOKKO CHEMICAL INDUSTRY CO., LTD; EP307106; (1989); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, belongs to ethers-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 5414-19-7, Product Details of 5414-19-7

(23a) A solution of methyl cyanoacetate (5.0 g, 50.6 mmol), 2-bromoethyl ether (16.9 g, 65.7 mmol), and potassium carbonate (17.5 g, 126.4 mmol) in acetone (100 mL) was heated at reflux overnight. The mixture was cooled, filtered, and concentrated to provide the desired pyran. The crude material was carried on as is.

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, 1-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
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Some common heterocyclic compound, 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, molecular formula is C9H10BrFO, 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. SDS of cas: 202865-80-3

Intermediate 12 2-(3-fluoro-4-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane :Potassium acetate (10.52 g, 107.2 mmol) and bis(pinacolato)diboron (15 g, 58.96 mmol) were added to a solution of intermediate 11 (10.52 g, 107.2 mmol) in dioxane (125 ml), and the solution was degassed for 30 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (4.4 g, 5.36 mmol) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate :petroleum ether to afford the title compound as a yellow oil (13.9 g, 99%) which was used without purification in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 202865-80-3, its application will become more common.

Reference:
Patent; Rhizen Pharmaceuticals SA; US2012/289496; (2012); A1;,
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Related Products of 157869-15-3, The chemical industry reduces the impact on the environment during synthesis 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, I believe this compound will play a more active role in future production and life.

General procedure: 2-(phenylethynyl)aniline (302.8 mg, 1.57 mmol, 1.0 equiv) was dissolved in DCM (5.0 mL) and cooled to 0 C. The solution was then added with Et3N (0.24 mL, 174.1 mg, 1.72 mmol, 1.1equiv), followed by acetyl chloride (0.18 mL, 198.0 mg, 2.52 mmol, 1.6 equiv). The resulting reaction mixture was allowed to stir at 0 C while slowly warming to room temperature over 5 h,at which point the reaction was complete as indicated by TLC. The reaction mixture was byaddition of water. The separated aqueous phase was extracted with DCM (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude solid. The crude solid product was purified by SiO2 column chromatography eluting with 20% EtOAc-hexane to give 354.4 mg (96%) of compound 1a as awhite solid.

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, 2-((4-Methoxyphenyl)ethynyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chaisan, Nattawadee; Kaewsri, Wilailak; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak; Tetrahedron Letters; (2018); p. 675 – 680;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Intermediate 104a: diethyl 2-(3-(benzyloxy)propyl)malonate To a suspension of sodium hydride (1.05 g, 26 mmol) in tetrahydrofuran (40 mL), was added diethyl malonate (7g, 44 mmol). Once evolution of gas had ceased, ((3- bromopropxy)methyl)benzene (5 g, 22 mmol) was added. The reaction mixture was heated in a 90 deg C bath for 6 h, then cooled to ambient temperature. The reaction was diluted with diethyl ether (100 mL) and washed with water (100 mL). The aqueous layer was separated and extracted with diethyl ether (2 x 100 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica-gel chromatography with ethyl acetate and heptanes as eluent to provide the desired compound. H NMR (400 MHz, CDCI3) delta 7.31-7.38 (m, 4H), 7.25-7.31 (m, 1 H), 4.50 (s, 2H), 4.10-4.27 (m, 7H), 3.50 (t, =6.3 Hz, 2H), 3.32-3.41 (m, 2H), 1.93-2.08 (m, 2H), 1.60 – 1.73 (m, 2H), 1.20- 1.38 (m, 10H) ppm.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARYZA, Jeremy Lee; BECKWITH, Rohan Eric John; BOWMAN, Keith; BYERS, Crystal; FAZAL, Tanzina; GAMBER, Gabriel Grant; LEE, Cameron Chuck-Munn; TICHKULE, Ritesh Bhanudasji; VARGEESE, Chandra; WANG, Shuangxi; WEST, Laura; ZABAWA, Thomas; ZHAO, Junping; WO2014/136086; (2014); A1;,
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