Ethers-buliding-blocks

Reference of 24988-36-1, 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 24988-36-1 as follows.

Into a 200-mL three-neck flask were put 7.1 g (24 mmol) of 1,5-dibromo-2,4-dimethoxybenzene, 2.8 g (20 mmol) of 2-fluorophenylboronic acid, 12 mL of toluene, 12 mL of diethylene glycol dimethyl ether, and 50 mL of a sodium carbonate aqueous solution (2 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.55 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 3 hours. After the mixture was cooled down to the room temperature, 4.5 g (32 mmol) of 2-fluorophenylboronic acid and 0.12 g (0.29 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl were added to the mixture and then the mixture was degassed under reduced pressure. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. again. After that, 30 mg (0.13 mmol) of palladium(II) acetate was add ed to the mixture, and stirring was performed at the same temperature for 4 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) to give 7.2 g (22 mmol) of a target pale yellow oily substance at a yield of 92%. A synthesis scheme of the above synthesis method is shown in (B-2) below.

According to the analysis of related databases, 24988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. Recommanded Product: 2-(2-Chloroethoxy)acetic acid

In a three-necked round-bottom flask under nitrogen atmosphere equipped with a mechanical stirrer, a thermometer, a condenser and a dropping funnel 6.87 g (0.05 mol) phosphorus trichloride and 10.75 g (0.05 mol) Amberlyst-15 (hydrogen form, dry) were mixed with 50 ml chlorobenzene . Slowly 6.90 g of (0.05 mol) 5-chloro-3- oxapentanoic acid was added drop-wise. After completed addition the reaction mixture was heated to 50 °C for 4 h. During the addition and reaction time the evolution of CO was observed. Then 10 ml water was added and the Amberlyst- 15 was filtered off. The solution was analyzed by ChiEta- and 31P-NMR spectroscopy and 4-Chloro-2-oxabutanyl-l-phosphonic acid observed at 58.9 percentw/w.

The synthetic route of 2-(2-Chloroethoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STRAITMARK HOLDING AG; BURCK, Sebastian, R., W.; NOTTE, Patrick; WO2013/17564; (2013); A2;,
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Related Products of 15799-79-8, 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. 15799-79-8 name is 3-Methoxy-N,N-dimethylaniline, 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.

[0147] (S)-3-(4-Dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol: To a 50-mL roundbottom flask equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (0.394 g, 1.60 mmol, 0.100 equiv), CH2Cl2 (16.0 mL), HCl (as a 4N solution in 1,4-dioxane, 0.400 mL, 1.60 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (4.69 mL, 32.0 mmol, 2.00 equiv). The reaction vessel was cooled to 0o C. before the addition of cinnamaldehyde (2.06 ml, 16.0 mmol, 1.00 equiv). The solution was stirred for 12 h at 0o C. and then warmed to ambient temperature and stirred for an additional 6 h. At that time, the reaction mixture was added drop-wise to a stirring suspension of NaBH4 (0.750 g, 0.198 mmol, 1.24 equiv) in ethanol. After 5 min, the reduction was quenched with saturated aqueous NaHCO3 solution and diluted with CH2Cl2. The layers were separated and the organic was washed with saturated aqueous NaHCO3 and brine solutions. The resulting solution was dried over sodium sulfate and concentrated in vacuo to give a pale yellow residue, which was purified by silica gel chromatography. Gradient elution with 25-50% EtOAc in hexanes afforded the product as a colorless oil in 81% yield (3.70 g, 13.0 mmol); 74% ee. 1H NMR (300 MHz, CDCl3) ?7.32-7.12 (m, 5H, ArH), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.7, 8.8 Hz, 1H, ArH), 6.27 (d, J=2.2, Hz, 1H, ArH), 4.51 (dd, J=6.6, 8.8 Hz, 1H, ArCH), 3.83 (s, 3H, OCH3), 3.65-3.48 (m, 2H, CH2OH), 2.93 (s, 6H, N(CH3)2), 2.38-2.12 (m, 2H, CHCH2), 1.98 (br s, 1H, OH); 13C NMR (75 MHz, CDCl3) ?157.8, 150.5, 145.5, 128.8, 128.4, 128.2, 125.9, 121.3, 105.5, 96.6, 61.6, 55.9, 41.1, 38.7, 38.2. [0148] The enantiomeric ratio of the product was determined by HPLC analysis using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=12.9 min, S isomer tr=18.1 min.

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

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)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 54149-17-6, Recommanded Product: 54149-17-6

A mixture of 5-nitro-1,2-dihydro-indazol-3-one (399 mg, 2.22 mmol), 1-bromo-2-(2-methoxy-ethoxy)-ethane (454 uL, 3.34 mmol), potassium iodide (370 mg, 2.22 mmol) and 1N sodium hydroxide solution (6.7 mL, 6.7 mmol) in 2 ml dioxane was stirred at 60 C. overnight. The reaction mixture was then cooled, poured into 50 mL H2O and 300 muL 10N NaOH was added. The aqueous layer was extracted with CH2Cl2 and then acidified to pH 2 with 6N HCl. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography to afford the product 1-[2-(2-methoxy-ethoxy)-ethyl]-5-nitro-1,2-dihydro-indazol-3-one (380 mg, 61%). ES-MS calcd for C12H15N3O5 (m/e) 281.26, obsd 282.17 (M+H).

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-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bolin, David Robert; Cai, Jianping; Cheung, Adrian Wai-Hing; Goodnow, JR., Robert Alan; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Yun, Weiya; US2009/76275; (2009); A1;,
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Electric Literature of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jizhen; Xu, Wenbin; Ding, Junshuai; Lee, Kuo-Hsiung; Tetrahedron Letters; vol. 57; 11; (2016); p. 1205 – 1209;,
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Application of 39021-83-5, These common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, 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.

2-(bromomethyl)-1,4-dimethoxy-3-methylbenzeneInto a 50-mL round-bottom flask, was placed a mixture of 1,4-dimethoxy-2,3-dimethylbenzene (1.00 g, 6.02 mmol, 1.00 equiv)(Example 128), CCl4 (20 mL), NBS (1.20 g, 6.74 mmol, 1.10 equiv) and BPO (145 mg, 0.57 mmol, 0.10 equiv). The solution was stirred for 16 h at 80 C. After concentration, the residue was diluted with 50 mL of TBME and washed with 3×20 mL of brine. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. This resulted in 1.20 g (81%) of 2-(bromomethyl)-1,4-dimethoxy-3-methylbenzene as a brown crude solid.

Statistics shows that 1,4-Dimethoxy-2,3-dimethylbenzene is playing an increasingly important role. we look forward to future research findings about 39021-83-5.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
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These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, 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. Recommanded Product: 1516-96-7

A -78 C. solution of 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (2.142 g; 7.158 mmol) in dry THF (15 mL) was treated with n-butyllithium (7.00 mL, 1.13M in hex, 7.88 mmol). The solution was stirred at -78 C. for 15 min, then treated with trimethylborate (976 muL; 8.59 mmol). The reaction was allowed to warm to ambient temperature and evaporated to a thick oil.

The synthetic route of 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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.

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 × 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in a compound 7e (29.5 mg, 100 mumol),1-ethynyl -3,5-dimethoxy-benzene (40.6 mg, 250 mumol), CuSO4 (3.2 mg, 20 mumol) and Na. ascorbate (20.0 mg, 100mumol) theOf the desired compound was prepared using. After stirring at room temperature the reaction mixture for 66 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 30: 1 CH2Cl2 / MeOH) Compound 2e by using as a brown solid form (23.1mg, 51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Application of 349-65-5, A common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

According to Method C4, 2-methoxy-5-(trifluoromethyl)aniline was reacted with phosgene followed by 3-(-2-(N-methylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 12: 4-Chloropyridine-2-carbonyl chloride HCl salt was reacted with ammonia according to Method A2, Step 3b to form 4-chloro-2-pyridinecarboxamide.

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2002/165394; (2002); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
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