Ethers-buliding-blocks

2930-05-4, 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. 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97%recovery) for further use.

The synthetic route of 2930-05-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shah, Arpan K.; Prathap, K. Jeya; Kumar, Manish; Abdi, Sayed H.R.; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 469; (2014); p. 442 – 450;,
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The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life. 1535-75-7

2-Trifluoromethoxyaniline (0.8Og, 5.0mmol) and sodium hydride (60% dispersion in mineral oil, 1.7eq) were stirred in dry DMF at room temperature for 2 hours, and 5-bromo- 2-chloropyridine (1.0Og, 5.0mmol) was added and the mixture stirred at room temperature overnight. Iced water was added slowly to the mixture, and the mixture was extracted with DCM (3x). The DCM was washed with 2M HCl solution (2x), dried (MgSO4), and concentrated. The residue was purified by column chromatography eluting using a gradient (EtOAc/hexanes 1 :9 v/v).

The chemical industry reduces the impact on the environment during synthesis 1535-75-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; DAVIS, Paul James; WO2010/57833; (2010); A1;,
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22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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.

General procedure: N-formylation of amines by CO2 and DMAB in the presence of UiO-66 as a catalyst was carried out in autoclave. The synthesis of formamides is as follows, Amines (5.0 mmol), UiO-66 (10 mg), DMAB (1.5 equiv.), DMF (7 mL) were added in the reactor at room temperature, reactor was closed, flushed two to three times by CO2 and 1 MPa CO2 pressure was introduced into reactor, then the reactor was heated to required temperature with continuous stirring. After the reaction was complete, the reactor was cooled, and the CO2 pressure was carefully discharged from the autoclave. The UiO-66 MOF was separated by centrifugation. The resultant mixture was concentrated by rotary evaporator and subjected to the column chromatography with ethyl acetate-petroleum ether used as an eluent to obtain the product. All the products are confirmed by GCMS.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Phatake, Vishal V.; Mishra, Ashish A.; Bhanage, Bhalchandra M.; Inorganica Chimica Acta; vol. 501; (2020);,
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The chemical industry reduces the impact on the environment during synthesis 2252-44-0, name is 3-(Trifluoromethoxy)bromobenzene, I believe this compound will play a more active role in future production and life. 2252-44-0

EXAMPLE 92 (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-({4-[3-(trifluoromethoxy)phenyl]piperazin-1-yl}carbonyl)propanenitrile (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile (377 mg, 0.913 mmol), meta-trifluoromethoxy bromobenzene (200 mg, 0.830 mmol), sodium tert-butoxide (111 mg, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (0) (22.8 mg, 0.025 mmol), racemic BINAP (31 mg, 0.05 mmol), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80 C. overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgSO4, filtered, evaporated, and purified on slica gel (10% hexanes/CH2Cl2) to yield 255 mg of the title compound as a white powder. 1H NMR 500 MHz (DMSO-D6): delta 7.97 (d, 1H, J=7.18 Hz), 7.88 (m, 1H), 7.84 (m, 1H), 7.78 (d, 1H, J=8.25 Hz), 7.52 (t, 1H, J=7.48 Hz), 7.41 (m, 2H), 7.30 (t, 1H, J=8.25 Hz), 7.23 (td, 1H, J=7.79 Hz, 1.68 Hz), 7.12 (m, 2H), 6.91 (dd, 1H, J=8.40 Hz, 1.68 Hz), 6.79 (m, 2H), 6.72 (d, 1H, J=8.09 Hz), 6.01 (s, 1H), 4.01 (s, 3H), 3.68 (bs, 4H0, 3.16 (bs, 4H) 1.63 (s, 3H) MS (ESI) m/z 574 ([M+H]+); Anal. calcd for C33H30F3N3O3. 0.35 C6H14: C, 69.82; H, 5.83; N, 6.96. Found: C, 69.81 H, 5.91; N, 6.74.

The chemical industry reduces the impact on the environment during synthesis 2252-44-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2005/256132; (2005); A1;,
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1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 methyl 2-cyanoacetate (0.89 mL, 10.1 mmol) inDMF (20 mL) at rt was added sodium hydride (0.97 g, 24.2 mmol),and the reaction mixture was stirred at rt for 15 min. Tetrabutylammoniumiodide (0.37 g, 1.0 mmol) and ((2-bromoethoxy)methyl)benzene (3.35 mL, 21.19 mmol) were added, and the reactionmixture was stirred at 90 C for 3 h. Water was added and theaqueous layer was extracted with ether (3). The combinedorganic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was concentrated togive the crude product. The crude product was purified by silicagel chromatography eluting with 0?30percent EtOAc/hexanes to give14 (2.4 g, 65percent yield) as a colorless oil. 1H NMR (500 MHz, CDCl3)d 7.41?7.27 (m, 10H), 4.49 (s, 4H), 3.78?3.69 (m, 5H), 3.45 (s,3H), 2.49?2.40 (m, 2H), 2.06 (dt, J = 14.2, 4.7 Hz, 2H). LC/MS m/z:(M+H)+ calcd for C22H26NO4, 368.19; found 368.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-37-9, its application will become more common.

Reference:
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
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74137-36-3, 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. 74137-36-3 name is 1,3-Dibromo-5-methoxybenzene, 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: 3-Bromo-5-methoxy-1 ,1 ‘-biphenyl was synthesised according to general procedures GP13 – from 1 ,3- dibromo-5-methoxybenzene (6.50 g, 24.4 mmol), phenylboronic acid (2.08 g, 17.0 mmol), Pd(PPh3)4 (1 .40 g, 5 molpercent), Na2C03 (6.47 g, 61 .0 mmol), toluene (70 ml_), ethanol (7.0 mL) and water (7.0 ml_); 100 ¡ãC, 16 h. Chromatographic purification (hexane) afforded a colourless oil (4.1 g, contained a small amount of impurity), which is used in the subsequent transformation as an impure mixture. H NMR of a pure chromatography fraction (400 MHz, DMSO-c/6) delta: 7.55-7.53 (m, 2H), 7.43-7.42 (m, 2H), 7.37 (d, J = 7.3 Hz, 1 H), 7.32-7.31 (m, 1 H), 7.03 (d, J = 1 .4 Hz, 2H), 3.85 (s, 3H). General procedures GP13 [00693] A mixture of bromide GP13_1 , Pd(PPh3)4, ArB(OR’)2, Na2C03, H20, EtOH and toluene was degassed with argon and then stirred at 100 ¡ãC for 16 h. After cooling to rt, the mixture was diluted with Et20 and filtered through celite. The organic solution was washed with H20, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography to afford biaryl GP13_2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
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70627-52-0, Adding a certain compound to certain chemical reactions, such as: 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, 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 70627-52-0.

Example 10 Process for the Preparation of 3-[5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoyl]-4-phenyl-oxazolidin-2-one 18 ml of Dichloromethane was added to 2.1 ml of TiCl4 at 20-25 C. under nitrogen atmosphere Cooled the reaction mass to 0 C., 2 ml of Ti(O-ipr)4 was added and stirred for about 15 minutes. To the reaction mass 50 ml Dichloromethane, 10 gms of 1-[5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoyl]-5-phenyl-pyrrolidin-2-one and 13.7 gms of Imines were added at 20-25 C. under nitrogen atmosphere. The reaction mass was cooled -30to -35 C. and 5.8 gms of Diisopropyl ethyl amine was added. Stirred the reaction mass for about 15 minutes and TiCl4 solution was added. Stirred the reaction mass for about 2-3 hours at -30to -35 C. and 60 ml of isopropyl alcohol was added followed by 50 ml of Dichloromethane and stirred the reaction mass for about 60 minutes, 6% Tartaric acid solution was added to the reaction mass at 20-25 C. and stirred for about 2 hours. Separate the organic layer and extract the reaction mass with 100 ml of dichloromethane. Combined the organic layers and washed with H2O followed by brine solution. Separated the organic layer and dried over Sodium Sulfate. Distilled the solvent completely under reducing pressure at 50-55 C. and 500 ml of methanol was added. Stirred the reaction mass for about 1-2 hours at 20-25 C., filtered the compound, washed with methanol and dried at 60-65 C. to get 8 gms of 3-[5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoyl]-4-phenyl-oxazolidin-2-one.

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, N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mylan Laboratories Limited; Husain, Mofazzal; G.S.C., Srikanth; Thorpunuri, Swapna; Datta, Debashish; (11 pag.)US2016/280642; (2016); A1;,
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A common compound: 1484-26-0, name is 3-Benzyloxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1484-26-0

General procedure: BSB-Cl 2 (314 mg, 1.2 mmol) and aniline 1 (1mmol) were premixed in THF (10 ml) at0 C to which was added LiHMDS (2 ml, 2 mmol). The resulting mixture was stirred for2 h at this temperature. Upon reaction completion, the solution was concentrated. Theresidue was purified with basic alumina flash chromatography to afford pure product

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, 1484-26-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lu, Erhu; Yadav, Arun; Weaver, Donald F.; Reed, Mark A.; Synlett; vol. 24; 17; (2013); p. 2259 – 2262;,
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Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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. 1484-26-0

A mixture of triethyl orthoformate (92 milliliters (mL), 0.55 mole (mol)) and 2,2-dimethyl-[1,3]-dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at 55¡ã C. for 90 minutes and then cooled to 45¡ã C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period of 45 minutes while maintaining the reaction temperature below 50¡ã C. The reaction was then heated at 45¡ã C. for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1¡ã C., and the product was isolated by filtration and washed with cold ethanol (400 mL) until the filtrate was colorless. 5-{[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (170.65 g) was isolated as a tan, powdery solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1484-26-0, its application will become more common.

Reference:
Patent; Zarraga, Isidro Angelo E.; US2007/166384; (2007); A1;,
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29578-83-4, A common compound: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

). 1-Bromo-3-methoxy-5-methylbenzene (1.00 g, 5.0mmol) and pyridine/H2O (2:5, 30 mL) were added to a round-bottomflask, followed by KMnO4 (3.14 g, 20 mmol). The resulting mixturewas then heated while refluxing for 48 hr. After the removal of the precipitateby filtration, 2 M HCl was added to the reaction mixture to acidify it (pH 2).The aqueous phase was extracted with ethyl acetate. The organic phase waswashed with brine and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure and the residue was purified usingsilica gel column chromatography. The white solid (385 mg, 34% yield) wasidentified as 3-bromo-5-methoxybenzoic acid (3a) on the basis of 1H-NMR spectra. 1H-NMR(400 MHz, CDCl3): d3.86(s, -OCH3, 3H), 7.29 (t, J=2.0Hz, Ar H, 1H), 7.54 (t, J=2.0 Hz, ArH, 1H), 7.83 (t, J=2.0 Hz, Ar H, 1H).

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-3-methoxy-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ohe, Tomoyuki; Umezawa, Ryutaro; Kitagawara, Yumina; Yasuda, Daisuke; Takahashi, Kyoko; Nakamura, Shigeo; Abe, Akiko; Sekine, Shuichi; Ito, Kousei; Okunushi, Kentaro; Morio, Hanae; Furihata, Tomomi; Anzai, Naohiko; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3708 – 3711;,
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