Category: ethers-buliding-blocks

Reference of 101-84-8, 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. 101-84-8, name is Diphenyl oxide belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6; Preparation of Partially brominated DPO[0056] To the 500 mL flask (equipped as described in Example 4) containing 47.3 g of DPO was added over about 10 minutes, 28.0 g of bromine with stirring and cooling at room temperature. Catalyzed Bromination [0057] In a 1 -liter jacketed flask equipped with mechanical stirrer, Friedrich condenser(water cooled at about 250C), and with a 1/32-inch diptube but without a fractionation column were placed 3.8 g of AlCl3 and 885 g of bromine. After a feed time of about 7.25 hours, all of the partially brominated DPO had been fed from the flask. The reaction temperature was maintained at 56.30C to 57.20C throughout the addition. The reaction mixture was refluxed for 4 minutes as the temperature rose to 58.40C, then 450 mL of water was added and the reactor was set for distillation. The product was distilled to 1700F (about 770C) and 312 g of bromine was collected. The water layer was decanted from the reactor, 400 mL of water was added, stirred, and discarded. Then 400 mL of water and 10 g of NaOH were added, the mixture was stirred well and product was collected and water washed on a filter. GC analysis showed the product was composed of 99.71% of decabromodiphenyl oxide, and 0.034 and0.259% of the first and second nonabromodiphenyl oxide isomers, respectively. The product was placed in a 1250C oven and after drying overnight weighed 252.0 g. EXAMPLE 7Preparation of Partially brominated DPO [0058] To the 500 mL flask (equipped as described in Example 4) containing 49.1 g of DPO was added over aboutlO minutes, 29.7 g of bromine. This was purged with nitrogen to remove HBr. Catalyzed Bromination[0059] In a 1 -liter jacketed flask equipped as in Example 6 (no fractionation column) were placed 3.8 g of AlCl3 and 884 g of bromine. The mixture was heated to 59C and a feed of the partially brominated DPO formed above was initiated. The feed through the 1/32-inch diptube was set at a rate of about 0.21 mL per minute. All the partially brominated DPO was added over 3 hours and 23 minutes, The reaction mixture had been maintained at a temperature of 56.10C to 57.10C throughout the addition time reflux was continued for about 10 more minutes as the temperature rose to 59.60C. Then 450 mL of water was added to the reaction mixture and the reactor was set for distillation. The mixture was distilled to 770C and 294.5 g of bromine was collected. The mixture was worked up as in Example 6. GC analysis of the product showed 99.59% of decabromodiphenyl oxide and 0.11% and 0.296% of first and second nonabromodiphenyl oxide peaks, respectively. Present in the product were a few “lumps”. One was removed and a GC showed it contained 99.61% of decabromodiphenyl oxide and 0.100 and 0.291% of the first and second nonabromodiphenyl oxide isomers, respectively. The product was oven dried. EXAMPLE 8Preparation of Partially brominated DPO [0060] To the 500 mL flask (equipped as in Example 4) containing 49.00 g of DPO was added 31.4 g of bromine over about 10 minutes. Then the mixture was purged with nitrogen. Catalyzed Bromination[0061] In a 1 -liter jacketed flask, equipped as in Example 6, were placed 3.82 g OfAlCl3 and 988 g of bromine The mixture was heated to 56.O0C and addition of the partially brominated DPO begun at a feed rate of about 0.18 mL per minute. This feed was maintained for a period of about 4 hours with the temperature fluctuating between 53.O0C and 54.O0C. The mixture was allowed to reflux for about another 7 minutes with the temperature reaching about 600C. Then, 450 mL of water was added to the reaction mixture and the reaction vessel was set for distilling bromine. The distillation was conducted to 770C whereby an amount of 400.2 g of bromine was recovered. Product was isolated as in Example 5 and oven dried. GC analysis showed 0.093% and 0.471% of the first and second nonabromodiphenyl oxide peaks, respectively, and 99.436% of decabromodiphenyl oxide. After drying over the weekend the product weighed 260.1 g.

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, Diphenyl oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBEMARLE CORPORATION; WO2008/27776; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

321-28-8, name is 1-Fluoro-2-methoxybenzene, 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. Computed Properties of C7H7FO

(A) 3-fluoro-4-methoxybenzaldehyde. To a solution of o-fluoroanisole, 101 g. (0.80 mole) in 500 ml. dry methylene chloride is added dropwise over 30 minutes a solution of titanium tetrachloride, 182 g. (0.96 mole, 1.2 equiv.) and alpha,alpha-dichloromethylmethyl ether, 110 g. (0.96 mole) in an equal volume of methylene chloride. The temperature is maintained at 10-20 C. with an ice-bath. The mixture is stirred at room temperature for 1 hour longer and then poured over crushed ice-water with stirring. Ether (1l.) is added, and the mixture stirred under nitrogen until solution occurs. The organic layer is extracted with water (3*), sodium bicarbonate solution (3*) and dried (MgSO4). The solvent is evaporated off at 30 to give crude product as an oil. The oil is vacuum distilled through a jacketed Vigreux column when it gives 3-fluoro-4-methoxybenzaldehyde, B.P. 120-121 C., at 10 mm. Hg; Rf 0.6 on a silica-gel G plate with methylene chloride.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Arizona; FGN, Inc.; US5401774; (1995); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 873980-68-8, 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 873980-68-8 as follows.

Preparation of 6-bromo-5-methybenzoxazole (43): To a suspension of 4-bromo-6-methoxy-3-methylaniline (41) (500 mg, 2.3 mmol) in 6 ml DCM was added 1 M BBr3 in DCM (4.6 ml, 4.6 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 581 mg 2-amino-5-bromo-4-methylphenol as dark oil.A mixture of 2-amino-5-bromo-4-methylphenol (42) (290 mg), trifluoromethanesulfonic acidYtterbium (III) salt (20 mg) and trimethyl orthoformate (185 mul, 1.5 eq.) in 2 ml EtOH was heated at 90 C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting brown solid was dissolved in DCM and subjected to silica gel column purification using 0-60% B (A: hexane; B: 50% EA in hexane) to furnish 91.9 mg 6-bromo-5-methylbenzoxazole (43) as yellow solid (yield: 38%)

According to the analysis of related databases, 873980-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 41864-45-3, These common heterocyclic compound, 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, 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.

The compound 63 (100 mg, 0.33 mmol) was dissolved in propionic acid (1 mL). 4,5-dimethoxy-2-methylaniline (223 mg, 1.33 mmol) was added to the solution. The mixture was stirred at 150C for 30 minutes. The reaction mixture was poured into ice water, and neutralized with the aqueous solution of sodium hydrogen carbonate. The mixture was extracted with ethyl acetate. The organic layer was washed by water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained oil was purified by silica-gel column chromatography (hexane-ethyl acetate). The obtained residue was solidified with ethyl acetate-hexane to give the compound 5 (66 mg, yield 47%). 1H-NMR (CDCl3) delta: 1.91 (s, 3H), 2.20 (s, 3H), 3.81 (s, 3H), 3.85 (s, 3H), 5.24 (br s, 2H), 5.38 (s, 1H), 6.26 (s, 1H), 6.70 (s, 1H), 6.50-6.85 (m, 2H), 7.52 (br s, 1H).

Statistics shows that 4,5-Dimethoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 41864-45-3.

Reference:
Patent; Shionogi & Co., Ltd; TANAKA, Satoru; OGAWA, Tomoyuki; KAI, Hiroyuki; OGATA, Yuki; HIRAI, Keiichiro; KUROSE, Noriyuki; FUJII, Yasuhiko; (438 pag.)EP3287443; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 31804-36-1, 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. 31804-36-1, name is 1-Bromo-3-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-l-methoxy-2-(3-methoxypropoxy)benzene (11.0 g, 54.7 mmol) in THF (120 mL) was added l-(2-thienyl)ethanone (8.97 g, 71.1 mmol), i-BuONa (7.89 g, 82.1 mmol), Pd2(dba)3 (1 g, 1.09 mmol) and Xantphos (633 mg, 1.09 mmol ) under nitrogen atmosphere. The mixture was heated at 50 C for 4 hrs, and then concentrated under reduced pressure. The residue was diluted with DCM (600 mL). The resulting organic mixture was washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography to afford 2-(3-methoxy-2-methyl- phenyl)-l-(2-thienyl)ethanone (13.0 g) as a brown oil.

The synthetic route of 1-Bromo-3-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; YANG, Song; (109 pag.)WO2016/128335; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 74654-07-2, 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. 74654-07-2 name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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.

Step a):Under inert atmosphere,5.00 g of 4-bromo-1,8-naphthalic anhydride was added to 100 mL of anhydrous methanol,1.96 g of 3,6,9-trioxa-1-aminodecane was further injected, and the mixture was refluxed for 10 hours.After the reaction was completed, overnight needle-like crystals were precipitated, filtered, washed with cold ethanol three times,The intermediate N-3,6,9-trioxadecyl-4-bromo-1,8-naphthalimide was obtained4.90 g (96% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Sci-Tech University; Han Yifeng; Chen Bo; Wei Ting; (13 pag.)CN105542756; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of intermediate compound (prepared ac- cording to teachings in WO99/58530 of which the content is included herein) (0.025 mol) and 2-phenoxyethanamine (0.036 mol) in THF (300 ml) was hydrogenated at 140 °C for 16 hours with Pd/C 10 percent (3 g) as a catalyst in the presence of thiophene solution (3ml). After uptake of H2 (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in 2-propanol. The precipitate was filtered off and dried. Yielding: 12.4 g of final compound 7 (94 percent).

The chemical industry reduces the impact on the environment during synthesis 2-Phenoxyethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 41789-95-1, A common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, molecular formula is C4H11NO2, 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. SDS of cas: 22483-09-6

Example 7A (2,2-Dimethoxy-ethyl)-carbamic Acid Benzyl Ester Benzyl chloroformate (Aldrich, 231.3 g, 1.3 mol) was added gradually to a mixture of aminoacetaldehyde dimethyl acetal (Aldrich, 152.0 g, 1.3 mol) in toluene (750 mL) and aqueous NaOH (72.8 g, 1.82 mol; in 375 mL of water) at 10-20 C. After the addition was complete, the mixture was stirred at ambient temperature for 4 h. The layers were separated and the organic layer was washed with brine (2*100 mL) and concentrated under reduced pressure to provide the title compound as an oil (281.5 g, 90% yield). 1H NMR (CDCl4, 300 MHz) delta 3.33 (t, J=6.0 Hz, 2H), 3.39 (s, 6H), 4.37 (t, J=6.0 Hz, 1H), 5.11 (s, 2H), 7.30 (m, 5H); MS (DCl/NH3) m/z 257 (M+NH4)+, 240 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22483-09-6, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyethoxy)ethanamine

PRODUCTION EXAMPLE 7 2-(2-methoxyethoxy)ethylguanidine 5.96 g (50.0 mmol) of 2-(2-methoxyethoxy)ethylamine and 3.00 g (50.0 mmol) of acetic acid were placed in a 30 ml two neck flask. While heating the flask in a 90 C. oil bath, 3.10 g (73.7 mmol) of cyanamide was added. After 5 hours of the reaction, the product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 3.15 g of the title compound (wax-like, 14.2 mmol, 28.5% in yield) in the form of acetate. Results of the analysis of this compound are as follows. 1 H-NMR (200 MHz, D2 O, TSP standard): delta 3.8 – 3.6 (m, 6 H), 3.45 – 3.30 (m, 5 H), 1.92 (s, 3 H) 13 C-NMR (50 MHz, D2 O, TSP standard) delta: 183.70, 160.06, 73.72, 72.24, 71.54, 60.77, 43.92, 26.06 IR (KBr, cm-1): 3348, 3104, 3084, 1686, 1650, 1554, 1456, 1406, 1356, 1304, 1246, 1202, 1100, 1018, 920, 846, 800, 760, 648

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; Kao Corporation; US5723133; (1998); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem