Tag: M.W=100-200

Application of 53145-38-3, These common heterocyclic compound, 53145-38-3, name is 2-Chloro-6-fluoroanisole, 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 1 : Synthesis, Isolation, and Use of PBA-diMe A solution of 2,6-CFA (15.2 g, 93.5 mmol) in anhydrous DME (118 mL) was prepared in a 500 mL bottle. Molecular sieves were added to remove water, and the water content was measured by Karl Fischer titration to assure water < 100 ppm (80 ppm measured). The solution was transferred to a reactor through a septum port and the septum was replaced. A nitrogen pad was started. An agitator was started and set at 270 rpm. A dewar dish under the reactor was filled half full with acetone solvent. Dry ice chunks were slowly added. When the bath solvent was cold more solvent was slowly added so the bath solvent level was above the level of the 2,6-CFA solution in the reactor. The bath was maintained at -76C during the experiment by adding dry ice chunks periodically. The 2,6-CFA solution was allowed to cool to -72C. w-BuLi in hexanes (2.5 M, 41.5 ml) was loaded into a 60 mL plastic syringe and positioned on a syringe pump. The syringe pump was started with an addition rate of 0.7 ml/min. The n-BuLi addition was complete after 64 minutes. The reaction solution was held as -72C for 57 minutes. B(OMe)3 (13. lg, 14.06 mL) was loaded into a 24 mL plastic syringe and positioned on the syringe pump. The agitator was increased to 302 rpm. With the reaction solution at -72C, the syringe pump was started with an addition rate of 0.4 mL/min. The borate addition was complete after 40 minutes. The reaction solution was left in the cold bath over night at 220 rpm agitation. A total of 153 g of the reaction solution containing PBA-diMe was collected. A GC method with an internal standard was used to quantify the amount of PBA-diMe in solution. A conversion to PBA-diMe of 98% was calculated with 2% of the original unconverted 2,6-CFA also quantified. The PBA-diMe solution was stirred at 18C in the reactor. The agitator was started and set to 294 rpm. C02 gas from a small lecture bottle was slowly bubbled into the solution through a inch (0.635 cm) glass tube over 42 minutes. The solution heated to 21 C. A total of 7.2 g (1.5 equivalents) of C02 gas was added. The mixture was very cloudy with fine white solids. The mixture (153 g) was filtered in a 7.5 cm Buchner funnel using 1 Whatman filter paper and a water aspirator. Fine white solids were removed (lithium methyl carbonate). 3.5 g of hexane was used to rinse the solids. 141 g of filtrate was collected. 3.5 g of dry white solids were collected. The PBA-diMe filtrate solution was place in a 500 mL round bottom flask on a roto-vap fitted with a water aspirator, dry ice trap, and an overhead receiver. The roto-vap was started with the bath at 25C. The vacuum ranged from 45 mmHg down to 15 mmHg and the final bath temperature was 31C. After 17 minutes 106.5 g of overhead solvent was collected and 30.1 g of bottoms remained. Analysis of the bottoms by GC gave 59.4 % by weight of PBA. The procedure resulted in 97 % recovery of PBA. Statistics shows that 2-Chloro-6-fluoroanisole is playing an increasingly important role. we look forward to future research findings about 53145-38-3. Reference:
Patent; DOW AGROSCIENCES LLC; OPPENHEIMER, Jossian; MENNING, Catherine A.; HENTON, Daniel R.; WO2013/101987; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, 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 886762-39-6, category: chlorides-buliding-blocks

1,2-Dichloro-3-fluoro-4-isothiocyanatobenzene A solution of sodium hydroxide (3 equiv.) in water (0.5 M) was added to a solution of 3,4-dichloro-2-fluoroaniline (1 equiv.) in DCM (1 M). The mixture was cooled to 0 C. and thiophosgene (3 equiv.) was added dropwise via syringe. The reaction mixture was allowed to warm to room temperature for 16 h. The mixture was extracted with DCM, the combined organic layers were dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography to afford 1,2-dichloro-3-fluoro-4-isothiocyanatobenzene (79%) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm: 7.24 (dd, J=8.8, 2.0 Hz, 1H), 7.06 (t, J=8.2 Hz, 1H).

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; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
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Application of 3972-56-3, 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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a 30 ml of two necked flask, 26.3 mg of PdCl2(PCy3)2, 667.8 mgof Cs2CO3 were introduced. To the mixture, 5ml of DMF, 168.7 mg of 4-tert-butyl-1-chlorobenzene, 368.6 mg of 2,5-norbornadiene and 170 mg of diethylenegycohol (internal standard) were added. The mixture was stirred for 6 hours at 120 ¡ãC. The mixture was cooled to ambient temperature and poured into 30 ml of water. The combined mixture was extracted with ether (50 ml, 3 times). The organic layer was washed with water and brine. The washed organic layer was dried over MgSO4, filtered and condensed in vacuo. The residue analyzed via GC quantitatively, using internal standard. Also the residue was chromatographed on SiO2 withhexane – ethyl acetate to give 6-tert-butyl-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene (2) in 62percent yield. The purified compound was determined its chemical structure with NMR analysis.

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

Reference:
Article; Aida, Fuyuki; Sone, Hisashi; Ogawa, Ryuhei; Hamaoka, Takeharu; Shimizu, Isao; Chemistry Letters; vol. 44; 5; (2015); p. 715 – 717;,
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Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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 4584-46-7, Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

1) Production of N,N-dimethyl-2-(5-nitro-2,3-dihydro-1H-indol-1-yl)ethylamine: 730 mg of sodium hydride was added to an N,N-dimethylformamide solution of 1 g of 5-nitroindoline, and stirred at room temperature for 30 minutes. 1.8 g of 2-dimethylaminoethyl chloride hydrochloride was added to the reaction liquid, and stirred at 70C for 1 hour. The reaction liquid was cooled, diluted with chloroform, and washed with aqueous saturated sodium bicarbonate solution and saturated saline water in that order. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting crude product was purified through basic silica gel column chromatography (chloroform/methanol) to obtain 950 mg of the entitled compound as a yellow oil. 1H-NMR (CDCl3) delta: 8.26 (1H, dd, J=8.8, 2.4 Hz), 8.14 (1H, d, J=2.4 Hz), 6.96 (1H, d, J=8.8 Hz), 3.88 (2H, t, J=6.8 Hz), 3.64 (2H, s), 2.57 (2H, t, J=6.8 Hz), 2.30 (6H, s) ESI-MS Found: m/z [M+H] 250

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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., Recommanded Product: 108-70-3

1,3,5-Trichlorobenzene (3.63 g, 20 mmol) and anhydrous THF (74 mL)were stirred under argon at -78 C and n-BuLi (18 mL, 0.9 M, 16.2mmol) was added dropwise over 30 min. The reaction mixture wasstirred for 1 h. A solution of acetaldehyde (1.76 g, 40 mmol) in anhydrousTHF (2 mL) was added to the mixture dropwise. The reactiontemperature was held at -78 C for 1 h. After 1 h, the reaction wasquenched with H2O and the mixture was transferred to a separatoryfunnel. The organic layer was separated, dried (MgSO4), concentratedby rotary evaporation, and high vacuum to completely remove thevolatiles. The crude product was then submitted to silica gel columnchromatography with hexanes to remove starting material and thenCH2Cl2 to provide the pure alcohol as a colorless oil; yield: 3.66 g(99%).1H NMR (400 MHz, CDCl3): delta = 7.32 (s, 2 H), 5.60-5.50 (dq, J = 6.9, 9.9Hz, 1 H), 2.81 (d, J = 9.9 Hz, 1 H), 1.62 (d, J = 6.9 Hz, 3 H).13C NMR (100 MHz, CDCl3): delta = 137.3, 134.4, 133.5, 129.2, 67.8, 21.3.

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

Reference:
Article; Miller, Daniel K.; Bailey, Christopher A.; Sammelson, Robert E.; Synthesis; vol. 47; 18; (2015); p. 2791 – 2798;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 103889-37-8, These common heterocyclic compound, 103889-37-8, name is 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene, 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 mixture of l-chloro-3-fluoro-2-(trifluoromethyl)benzene (2 g, 10 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise 2 M lithium diisopropylamide (2.0 M in tetrahydrofuran/n-heptane, 7.6 mL, 15 mmol). The mixture was stirred for 1 hour, and then N, N-dimethylformamide (0.9 g, 12 mmol) was added dropwise at -70 C. The reaction was stirred at -70 C for another 1 hour, then quenched by addition of water (20 mL), acidified to pH 2 with concentrated hydrochloric acid at 0 C, and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated brine (3 x 10 mL), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give compound mixture B-185 (1.7 g, 11: 1 ratio of hydrate: aldehyde) as a yellow solid. -NMR (CD3OD, 400 MHz): delta 10.27 (s, 1H), 8.09-8.03 (m, 1H), 7.81 (t, J=8.0 Hz, 11H), 7.60 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.8 Hz, 11H), 5.75 (s, 11H). To a solution of compound mixture B-185 (0.5 g, 2 mmol) in dichloromethane (5 mL) was added triethylamine (0.3 g, 3 mmol) and methyl 2-sulfanylacetate (0.3 g, 3 mmol). The mixture was stirred at 40 C for 20 hours, then diluted with water (40 mL) and extracted with ethyl acetate (3 chi 40 mL). The combined organic layers were washed with brine (3 x 10 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10: 1] to give compound B-186 (0.4 g, 70% yield) as a white solid. -NMR (CD3OD, 400 MHz): delta 8.14 (d, J=6.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 1H), 3.96 (s, 3H).

Statistics shows that 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 103889-37-8.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-04-9, 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. 2106-04-9 name is 3-Chloro-2-fluoroaniline, 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.

EXAMPLE 3; Step 1 A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/-5 C. and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2¡Á40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (30 in Hg) at 40 C. for 8 hours to afford the compound of Formula 3B (71% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Muci, Alex; Lu, Pu-Ping; Morgan, Bradley P.; Morgans, JR., David J.; US2009/192168; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-4-fluorobenzylamine

Example 221-[(2-Chloro-4-fluorophenyl)methyl]-4-(2,6-dimethylphenyl)-2,3-piperazinedione(E22)Methyl [(2,6-dimethylphenyl)(2-oxoethyl)amino](oxo)acetate (0.27 g, 1.0 mmol) and 2-chloro-4-fluorobenzylamine (0.19 g, 1.2 mmol) were stirred in 2% acetic acid/methanol (10 ml) for 5 minutes, whereupon polymer-supported cyanoborohydride (0.98 g, 4.0 mmol) was added. The mixture was stirred at room temperature for 16 hours. The resin was filtered off using an SCX cartridge (Varian, 5g), washing through with methanol. The filtrate was concentrated in vacuo to afford the crude product as a gum. The crude material was purified twice by flash-silica gel chromatography (first eluting with a 0-25% gradient of methanol in dichloromethane; then re-purified using a 0-100% gradient of ethyl acetate in iso-hexane) to afford 1- [(2-chloro-4-fluorophenyl)methyl]-4-(2,6-dimethylphenyl)-2,3-piperazinedione (0.11 g)-LC/MS [M+H]+ = 361 , retention time = 2.78 minutes.

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; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 74483-46-8, These common heterocyclic compound, 74483-46-8, name is 2-Chloro-4-methyl-1-(trifluoromethyl)benzene, 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.

Step 1: 3-Chloro-4-trifluoromethylbenzylbromide 27 A mixture of 2-chloro-4-methyl-1-trifluoromethylbenzene 26 (0.20 g, 1 mmol), N-bromosuccinimide (0.17 g, 1 mmol) and benzoyl peroxide (7.4 mg, 0.03 mmol) in carbon tetrachloride (2 mL) was heated to reflux for 2 hours. Another portion of benzoyl peroxide (20 mg, 0.08 mmol) was added. The mixture was heated to reflux for another 0.5 hours. The reaction mixture was further stirred at room temperature for 16 hours. The solid was removed by filtration. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica, using petroleum ether as eluent, to give 0.22 g (80%) of Compound 27.

Statistics shows that 2-Chloro-4-methyl-1-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 74483-46-8.

Reference:
Patent; CanBas Co., Ltd.; US2008/275057; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-4,5-difluoroaniline

[ithium 1,1,1 ,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahydrofuran, 42 mmol, CAS No 4039-32-1) was added drop wise within 5 minutes to a solution of 2-chloro- 4,5-difluoroaniline (3.88 g, 23.2 mmol) in tetrahydrofuran (110 ml) at -780 and the mixture was stirred for 1 h at that temperature. A solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-1 – (2-chloroethyl)cyclohexanecarboxylate (10.0 g, 21.1 mmol) in tetrahydrofuran (110 ml) wasadded and the mixture was stirred for 2 h at -78G. The mixture was warmed to room temperature and stirred for 4 d. For work-up, the reaction mixture was added to a mixture of water and sodium bicarbonate solution and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washed with sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate). The productcontaining fractions were concentrated and were purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate) to give the title compound in 2 fractions: fraction 1 (7.53 g, single isomer based on 1H NMR, isomer 1, contains impurities from aniline and isomer 2), fraction 2(1.13 g, isomer2).Fraction 1 (isomer 1): 1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 7.67-7.55 (m, 5H), 7.52-7.30 (m, 9H), 3.97 (brs, 1H), 3.60 (t, 2H), 2.15-2.07 (m, 2H), 2.04 (t, 2H), 1.76-1.63 (m, 2H), 1.58- 1.45 (m, 2H), 1.39-1.27 (m, 2H), 1.05 (5, 9H).[C-MS (Method 1): R = 1.80 mm; MS (ESIpos): m/z = 518.3 [M¡ÂH]

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 2613-32-3.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics