Month: February 2021

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

Synthetic Route of 33863-76-2, 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 6TERT-BUTYL 3-(3-CHLORO-S-FLUOROPHENYL)-S-HYDROXYAZETIDINE-I – CARBOXYLATE5 A mixture of 1 -bromo-3-chloro-5-fluorobenzene (1.47 g, 7.01 mmol),, magnesium turnings (0.82 g, 31.1 mmol) and a small piece of iodine in dry tetrahydrofuran (50 mL), under nitrogen was gently heated until reaction started and stirred for 1 h at ambient temperature after which a solution of 1 -Boc-3-azetidinone (1.0 g, 5.85 mmol) in dry diethyl ether (10 mL) was added dropwise. The resulting10 mixture was stirred for 15 min and water (70 ml) and saturated aqueous ammonium chloride (20 mL,) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 :4 to 1 : 1 ) to give the title compound Yield: 1.25 g. MS m/z15 (rel. intensity, 70 eV) 285 (M+, 1 ), 156 (60), 141 (43), 127 (80), 57 (bp).

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

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; SONESSON, Clas; SWANSON, Lars; PETTERSSON, Fredrik; WO2010/58020; (2010); 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

Application of 174913-12-3,Some common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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 1-bromo-3-chloro-5-methoxy-benzene (800 mg, 3.61 mmol) and 1,4- dioxa-8-azaspiro[4.5]decane (500 mg, 2.78 mmol) in dioxane (20 mL) was added t-BuONa (668 mg, 6.95 mmol), Pd2(dba)3 (51 mg, 0.05 mmol) and Ruphos (52 mg, 0.1 mmol) under N2. After being heated with stirring at 100C overnight, the resulting reaction mixture was cooled to rt,diluted with H20 (20 mL) and extracted with EA (50 mL) for three times. The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 8 -(3-chloro-5-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (700 mg), which was used in the next step without further purification.

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-chloro-5-methoxybenzene, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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

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

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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, A new synthetic method of this compound is introduced below., name: 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

To a stirred solution of 4-bromo-l-chloro-2-(4-ethoxybenzyl)benzene (747 g, 2.31 mol) in dichloromethane was added boron tribromide (1.15 kg, 4.62 mol) slowly at -78 C. The reaction mixture was allowed to rise to room temperature. When the reaction was complete as measure by TLC, the reaction was quenched with water. The mixture was extracted with dichloromethane. The organic layer was washed with aqueous solution of saturated sodium bicarbonate, water, brine, dried over Na2S04, and concentrated. The residue was recrystallized in petroleum ether to give the title compound as a white solid (460 g, yield 68%). 1H NMR (CDC13, 400MHz): delta 7.23-7.29 (m, 3H), 7.08 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.8 Hz, 2H), 5.01 (s, 1H), 4.00 (s, 2H).

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; THERACOS, INC.; CAI, Mengzhuang; LIU, Qian; XU, Ge; LV, Binhua; SEED, Brian; ROBERGE, Jacques; WO2011/153712; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 14862-52-3, A common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

Compound (M-3) (270 g, 1.0 mol, 1.0 eq) was added to a 5 L four-necked round bottom flask under nitrogen protection.Compound (N-3) (122g, 1.0mol, 1.0eq) and 2500mL of toluene, then add sodium carbonate (212g, 2.0mol, 2.0eq) and purified water (360g, 20mol, 20eq), nitrogen purge for 30mins, then add Tetrakis (triphenylphosphine) palladium (11.5g, 0.01mol, 0.01eq), heated to 110 for 15hThe reaction was monitored by HPLC for completion. Filtered with diatomaceous earth, washed the organic phase with 2000 mL of saturated brine, and dried over anhydrous sodium sulfate. Distilled to 400 mL under reduced pressure, and 2000 mL of ethanol was added dropwise to precipitate most of the solid, filtered,Drying under vacuum gave 182 g of the target compound (D-3) as an off-white solid,Yield: 68%.

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Dinghao Optoelectric Materials Technology Co., Ltd.; Zhang Yuxiang; Zhang Qingyun; Ding Huanda; Chen Zhikuan; (41 pag.)CN110551154; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

General procedure: To a solution of 1-(3-Amino-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-propenone (1) (0.1 g, 0.373 mmol) in 2.5 mL of dioxane/H2O (50:50) was added methanesulfonyl chloride (0.043 g, 0.372 mmol) over a 20 min period at 0 C followed by 5 h of vigorous stirring at room temperature. The solvent was removed in vacuo, and the resulting solid was purified by silica gel column chromatography (CHCl3/methanol = 95:5).

The synthetic route of 6579-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Chong-Bin; Ahn, Chan Mug; Oh, Sangtae; Kwon, Daeho; Cho, Won-Chul; Shin, Woon-Seob; Cui, Yuan; Um, Ye Sol; Park, Byong-Gon; Lee, Seokjoon; Bioorganic and Medicinal Chemistry; vol. 23; 20; (2015); p. 6673 – 6682;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics