Month: June 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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-6-methoxynaphthalene

Under argon atmosphere, 2.37 g (0.01 mol) of 2-bromo-6-methoxynaphthalene and 40.578 g of Pd (PPh3)(0.5 mmol) of CuI, 0.095 g (0.5 mmol) of CuI and 30.131 g (0.5 mmol) of PPh. After the addition was completed, the mixture was purged with argon three times,Air was removed from the reaction flask, and then 15 ml of triethylamine, 1.96 ml of trimethylethynylsilane and 30 ml of tetrahydrofuran were added.After the addition was completed, the system was allowed to rise to 78 C for 20 h.The reaction mixture was filtered to remove a large amount of insoluble salts and solids. To the filtrate was added 150 ml of methylene chloride and the mixture was washed three times with 150 ml of 5% diluted hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Ether to do the agent.After the column liquid was swirled to a white solid precipitation stopped rotating when placed at room temperature precipitated a large number of white solid, filtered and dried to give a white solid6-Methoxy-2-naphthylethynyltrimethylsilyl2.50 g, yield 98.4%

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; East China University of Science and Technology; Shen Dong; Liu Haipeng; Zheng Zhigang; (18 pag.)CN106336350; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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. category: ethers-buliding-blocks

General procedure: General procedure for the preparation of arylalkynes 2a-q (non-decarboxylative approach, method A). An oven-dried 20 mL Schlenk tube equipped with a magnetic stirring bar and a rubber septum was charged with Pd(OAc)2 (6.7 mg, 30 mumol), tri(p-tolyl)phosphine (18.2 mg, 60 mumol). After purging the vessel with alternating vacuum and nitrogen cycles, degassed THF (3 mL), 1,8-diazabicycloundec-7-ene (450 muL, 3.0 mmol), 2-methylbut-3-yn-2-ol (120 muL, 1.24 mmol) and aryl bromides 1a-q (1.0 mmol) were added via a syringe (solid aryl bromides were added as solution in degassed THF) and the mixture was stirred at 80 C for 6 h. After cooling to rt the mixture was diluted with water (20 mL) and extracted with AcOEt (3 20 mL). Combined organic extracts were washed with H2O (20 mL), saturated aqueous NaCl (20 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel chromatography (eluant hexane/Et2O gradient) affording the corresponding products 2a-q.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Article; Caporale, Andrea; Tartaggia, Stefano; Castellin, Andrea; De Lucchi, Ottorino; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 384 – 393;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Computed Properties of C7H6F3NO

[00310] A reaction vial was charged with 2-benzyl-5-chloro-l,2,3,4-tetrahydro-2,6-naphthyridine(25.00 mg, 0.09662 mmol), 3-(trifluoromethoxy)aniline (42.8 mg, 0.000242 mol), tris(dibenzylideneacetone)dipalladium(0) (2.2 mg, 0.0000024 mol), xantphos (3 mg, 0.000005 mol), sodium tert-butoxide (14 mg, 0.00014 mol), and toluene (0.500 mL, 0.00469 mol) and tert-butyl alcohol (0.1 mL, 0.001 mol) and the vial was flushed with argon. The reaction mixture was then stirred at 110 0C in a microwave for 30 minutes. The reaction mixture was then filtered and solvent removed and the residue purified by prep HPLC to get the pure compound as a yellow solid. MS (M+H)= 400.4;1H-NMR (CDCl3): (400 MHz) 88.03 (d, 7=4.66 Hz, IH), 7.61 (bs, lH),7.48-7.44 (m, 2H), 7.40-7.28 (m, 5H), 6.83 (d, J=7.98 Hz, IH), 6.51 (d, 7=5.1 1 Hz, IH), 6.25 (bs, IH), 3.85 (s, 2H), 3.70 (s, 2H), 3.00 (t, J=5.50 Hz, 2H), 2.76 (t, 7=5.50 Hz, 2H)

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RENOVIS, INC.; WO2009/11904; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: To asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6851-80-5

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

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 6851-80-5.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C18H21NO4

Example 2 (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-((2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (10y) To a stirred solution of (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)aniline (5d) (100 mg, 0.317 mmol) in ethanol (5 ml) 1-(2-bromo-3,4,5-trimethoxyphenyl)prop-2-yn-1-one (6y) (94.9 mg, 0.317 mmol) was added. The reaction mixture was stirred at a temperature of 27 C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (1:1) as a solvent system. Then water (10 ml) was added to reaction mixture. A yellow colour solid appears which was filtered and washed with ethanol. (yield: 150 mg, 76%); mp: 108-110 C.; 1H NMR (CDCl3, 300 MHz) deltadelta (ppm): 3.94 (s, 3H), 3.91 (s, 3H), 3.90 (s, 3H), 3.87 (s, 3H), 3.84 (s, 3H), 3.70 (s, 6H), 5.64 (d, J=8.30 Hz, 1H), 6.49 (d, J=9.06 Hz, 4H), 6.81 (d, J=8.3 Hz, 1H), 6.87 (s, 1H) 6.97 (d, J=8.3 Hz, 1H), 7.14 (s, 1H), 7.28-7.19 (m, 1H), 11.92 (d, J=12.8 Hz, NH); FABMAS: (M+H)=614.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Council of Scientific and Industrial Research; Ahmed, Kamal; Gajjela, Bharath Kumar; Anver, Basha Shaik; Vangala, Santhosh Reddy; Mahesh, Rasala; US2015/322009; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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.

(RS)-1-(3-Bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol Magnesium turnings (981 mg) and a crystal of iodine were suspended in tetrahydrofuran (10 mL) at room temperature. To this was added ~5 mL of a solution of 4-bromo-2-methylanisole (7.1 g) in tetrahydrofuran (100 mL). The mixture was then heated at reflux until initiation (colour change from brown to colourless ~15-30 min) after which time the heat was removed. The remaining 4-bromo-2-methylanisole solution was added dropwise to maintain a gentle reflux and the resultant mixture was then heated at reflux for 2 h. Upon cooling to room temperature, a solution of 1-(3-bromo-2-fluorophenyl)-ethanone (7.3 g) in tetrahydrofuran (100 mL) was added dropwise, again maintaining a gentle reflux and this was then heated at reflux for 2 h before being allowed to cool to room temperature. The mixture was then poured onto ice-water (400 mL) and the solvent removed by evaporation. The product was extracted with ethyl acetate (3*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield a yellow oil. Purification by flash chromatography on silica (20:1-5:1 hexanes/ethyl acetate) yielded (R,S)-1-(3-bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol as a yellow oil (6.37 g, 56%). 1H NMR (CDCl3): 1.94 (3H, s, ArCH3), 2.17 (3H, s, ArCH3), 3.80 (3H, s, ArOCH3), 6.75 (1H, d, Ar), 7.00-7.16 (3H, m, Ar), 7.47 (1H, t, Ar), 7.63 (1H, t, Ar).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 25245-34-5, 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 25245-34-5 as follows.

General procedure: The Suzuki reaction was performed in a 50 mL round-bottomed flask, aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), Complex 1 (0.2-1 mol%) and water (4 mL) were charged and stirred for the required time at room temperature for aryl bromides or at 100 C for aryl chlorides. After completion, the mixture was cooled down to room temperature, diluted with water (10 mL) and extracted with diethyl ether (3 × 15 mL). The organic layer was washed with brine (3 × 15 mL), dried over anhydrous Na2SO4. The crude products were chromatographed on silica gel (ethyl acetate/hexane).

According to the analysis of related databases, 25245-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shahnaz, Nasifa; Puzari, Amlan; Paul, Bidisha; Das, Pankaj; Catalysis Communications; vol. 86; (2016); p. 55 – 58;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 1579-40-4, 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 1579-40-4 as follows.

An H-shaped reactor with two reaction chambers was purged with argon. A stirring bar (1.0 mm × 0.4 mm) was then located in each chamber of the reactor. Sulfuric acid (0.8 mL, 1.47 g, 15.0 mmol) was placed at the bottom of one chamber (chamber 1) of the reactor, and Galden HT-135 (1.0 mL) was slowly added to chamber 1 using a syringe. Subsequently, ammonium formate (443 mg, 7.0 mmol) was added, which formed a third layer in chamber 1. A solution of di-p-tolyl ether (13, 198.6 mg, 1.0 mmol), Pd(OAc)2 (5.5 mg, 2.5 mol%), and K2S2O8 (541.0 mg, 2.0 mmol) in trifluoroacetic acid (2.5 mL) was placed in the other chamber (chamber 2) of the reactor. Rubber septa were fitted to the reactor, and a needle equipped with a balloon was then pricked into the septum of chamber 2. The air in the reactor was withdrawn using a syringe until the balloon was completely flattened. The reactor was the heated in an oil bath at 45 C for 5 h under slow stirring, with care taken not to mix the layers in chamber 1, then allowed to cool to 25 C. The mixture in chamber 2 was transferred to an Erlenmeyer flask containing water using dichloromethane (DCM). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with brine then dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica-gel column chromatography using hexane/chloroform (1/4) as the eluent to afford desired product, 2,7-dimethylxanthen-9-one (14, 178.8 mg, 80%) as a white solid. 2,7-Dimethylxanthen-9-one (14) [S14] OCO2MeO S11 1H-NMR (400 MHz, CDCl3): delta 8.12 (2H, d, J = 0.9 Hz, ArH), 7.53 (2H, dd, J = 8.5, 2.1 Hz, ArH), 7.39 (2H, d, J = 8.7 Hz, ArH), 2.47 (6H, s, CH3); 13C-NMR (100 MHz, CDCl3): delta 177.36, 154.42, 135.94, 133.48, 126.02, 121.43, 117.75, 20.89.

According to the analysis of related databases, 1579-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adachi, Yusuke; Matsubara, Hiroshi; Journal of Fluorine Chemistry; vol. 216; (2018); p. 89 – 95;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, Application In Synthesis of (Triethoxymethyl)benzene

EXAMPLE III 1,5-diacetyl-3-(ethoxy-phenyl-methylidene)-2-indolinone 32.6 g (150 mmol) 1,5-diacetyl-2-indolinone are suspended in 100 ml triethyl orthobenzoate and stirred overnight with 150 ml acetic anhydride at 110° C. Then a further 50 ml triethyl orthobenzoate are added and the mixture is stirred for a further 24 h. Then it is evaporated down and the resulting precipitate is suction filtered, washed and dried. Yield: 38 g (72.5percent of theory) Rf=0.60 (silica gel, methylene chloride/methanol 30:1) C21H19NO4 (MW=349.384) Mass spectrum: m/z=350 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Triethoxymethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/234120; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem