Category: ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 583-19-7, name is 1-Bromo-2-ethoxybenzene, 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 583-19-7, Application In Synthesis of 1-Bromo-2-ethoxybenzene

Synthesis of Compound 67.2. [0740] Into a 100-mL 3-necked round-bottom flask was placed Mg (1.55 g) and 10 mL of tetrahydrofuran. Then 1-bromo-2-ethoxybenzene (1 g) and 1,2-dibromoethane (100 mg, 0.53 mmol, 0.01 equiv) were added to initiate the reaction. Then a second batch of 1-bromo-2-ethoxybenzene (9 g) were dissolved in 40 mL THF was added dropwise. The resulting solution was stirred for 2 h at room temperature. The mixture was directly used in the next step.

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

Reference:
Patent; Nimbus Apollo, Inc.; Harriman, Geraldine C.; Masse, Craig E.; Harwood, James; Bhat, Sathesh; Greenwood, Jeremy Robert; US2013/123231; (2013); A1;,
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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 1515-95-3 as follows. name: 1-Ethyl-4-methoxybenzene

General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 muL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 % aq tert-butyl hydroperoxide (200 muL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4).

According to the analysis of related databases, 1515-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hossain, Md. Munkir; Shyu, Shin-Guang; Tetrahedron; vol. 72; 29; (2016); p. 4252 – 4257;,
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Application of 54314-84-0, 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. 54314-84-0 name is ((3-Bromopropoxy)methyl)benzene, 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.

Synthesized according to the methods of general procedure 4 in U.S. Pat. Pub. No. 20090227541 (U.S. Pat. App. No. 12/142,692) using the following reactants and amounts: 2-bromo-3-hydroxy-4-methoxy-benzaldehyde (1.0 g, 4.32 mmol), (3- bromo-propoxymethyl)-benzene (0.76 mL, 4.32 mmol), cesium carbonate (2.11 g, 6.5 mmol), DMF (30 mL). Purification: flash chromatography (10percent EtOAc/hexanes): yield 1.54 g (95percent). 1H NMR (400 MHz, CDC13) delta (ppm): 10.26 (s, 1 H), 7.73 (d, J=8.6 Hz, 1 H), 7.46-7.18 (m, 5 H), 6.95 (d, J=8.6 Hz, 1 H), 4.56 (s, 2 H), 4.14 (t, J=6.1 Hz, 2 H), 3.92 (s, 3 H), 3.77 (t, J=6.2 Hz, 2 H), 2.15 (quin, J=6.5 Hz, 2 H); MS (ESI): m/z = 381 (M+l, positive).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, ((3-Bromopropoxy)methyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; DING, Charles; PLATTNER, Jacob, J.; ALLEY, Michael Richard, Kevin; ROCK, Fernando; ZHANG, Suoming; EASOM, Eric; LI, Xianfeng; ZHOU, Ding; WO2012/33858; (2012); A2;,
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Some common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-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. Recommanded Product: 1-Bromo-3-methoxy-5-methylbenzene

A mixture of 5-bromo-3-methoxytoluene (20 g, 0.1 m), N-bromosuccinimide (17.8 g, 0.1 m) and dibenzoyl peroxide in carbon tetrachloride (200 ml) is heated to reflux and irradiated with a sunlamp. The mixture is cooled, filtered and concentrated in vacuo to give 5-bromo-3-methoxybenzyl bromide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 29578-83-4, its application will become more common.

Reference:
Patent; SmithKline Beckman Corporation; US4659706; (1987); A;,
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767-91-9, name is 2′-Methoxyphenyl acetylene, 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. HPLC of Formula: C9H8O

General procedure: Ferric sulfate hydrate (I, 8 mol%), glacial acetic acid (5 mL) and the alkyne (1 – 2 mmol) were introducedinto a 50 mL Schlenk tube, equipped with an air condenser, and the mixture kept under stirring at 95 C or120 C, until consumption of the substrate or no further conversion, as evidenced by TLC or GC. Uponcooling, the supernatant solution was poored into water and the residue washed twice with diethyl ether.After extraction with diethyl ether ( 2), the combined organic layers were washed with a saturated aqueoussolution of sodium bicarbonate and then water until neutrality. Alternatively, the crude from the reactions ofsubstrates featuring hydroxyl or carbonyl groups, as for 12, 15, 20 and 22, was obtained by removing aceticacid under vacuum, in order to reduce loss of material during biphasic extraction. The products were purified

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bassetti, Mauro; Ciceri, Samuele; Lancia, Federico; Pasquini, Chiara; Tetrahedron Letters; vol. 55; 9; (2014); p. 1608 – 1612;,
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Application of 7664-66-6, 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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 54: Preparation of 2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5- oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(propan-2-yloxy)phenyl]acetamide. – EDCI (143 mg; 0.74 mmol; 1.5 eq), followed by HOBt (113 mg; 0.74 mmol; 1.5 eq), DIPEA (256 muU 1-49 mmol; 3 eq) and 4-(propan-2-yloxy)aniline (150 mg; 0.99 mmol; 2 eq) were added to a solution of 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl] -5-oxo-2-sulfanylideneimidazolidin-4-yl] acetic acid (1-21 ) (200 mg; 0.50 mmol; 1 eq) in anhydrous dioxane (8 mL). The reaction mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was purified on silica gel using dichloromethane/ethyl acetate (95/5) as an eluent. After trituration in diethyl ether/ethanol, the title compound 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(propan-2- yloxy)phenyl]acetamide was obtained with 43% yield (114 mg) as a white solid. 1H- NMR (Acetone-d6): delta (ppm), 1.26 (d, 6H), 2.94 (m, 1H), 3.15 (m, 2H), 3.36 (m, 1H), 3.74 (s, 3H), 3.78 (m, 1H), 4.31 (m, 1H), 4.59 (m, 2H), 6.86 (d, 4H) , 7.25 (m, 4H), 7.48 (m, 4H), 9.32 (s, 1H); MS (ESI+): m/z = 535.9 [M+H]+ .

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

Reference:
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
Ether – Wikipedia,
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These common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)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. name: (Triethoxymethyl)benzene

General procedure: Triethyl orthoformate, orthoacetate, orthopropionate or orthobenzoate(10 mmol) was added dropwise to the mixture of 1,2,4,5-tetrazine-3,6-dicarbohydrazide (6) (0.5 g, 2.5 mmol) and glacial aceticacid (7 mL). The reaction was carried out using conventional heating ormicrowave irradiation (150 W) in five cycles of 90 s with 2 min intervalsat the temperature 50-100 C.

The synthetic route of (Triethoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; K?dzia, Anna; Kudelko, Agnieszka; ?wi?tkowski, Marcin; Kruszy?ski, Rafa?; Dyes and Pigments; vol. 172; (2020);,
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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 6298-96-0 as follows. Computed Properties of C9H13NO

(a). ( 1 S)-JV- r 1 -(4-Methoxy-phenyl>ethyll -3 -oxo-butyramide; To a solution of (S)-l-(4-methoxy-phenyl)-ethylamine (25 g) in dichloromethane (60 mL) was added TEA (20 g) and DMPA (200 mg). Then a solution of 4-methylene- oxetan-2-one (16.7 g) in dichloromethane (60 ml) was added over a period of 30 minutes and then stirred at 20 0C for 18 h. The mixture was washed with IM HCl, aq. NaHCO3 and aq. NaCl. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. EPO Yield: 39.8 g. MS-ESI: [M+H]+ = 236

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2006/117368; (2006); A1;,
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Related Products of 2132-62-9,Some common heterocyclic compound, 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne, molecular formula is C16H14O2, 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: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(4-methoxyphenyl)ethyne, its application will become more common.

Reference:
Article; Kotla, Siva K. Reddy; Choudhary, Deepak; Tiwari, Rakesh K.; Verma, Akhilesh K.; Tetrahedron Letters; vol. 56; 32; (2015); p. 4706 – 4710;,
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Synthetic Route of 22483-09-6, The chemical industry reduces the impact on the environment during synthesis 22483-09-6, name is 2,2-Dimethoxyethanamine, I believe this compound will play a more active role in future production and life.

(3,4-Methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine (11b). Aminoacetaldehyde dimethylacetal (7.10 g, 0.0666 mol) was dissolved in chloroform (50 mL) and MgSO4 (12 g) was added. Then piperonal (10b, 10.10 g, 0.0666 mol) was added and the mixture was stirred at room temperature. After 24 h there still was unreacted piperonal in the reaction mixture and more amine (6.00 g) was added. The reaction mixture was stirred again at room temperature for 24 h and since there still was some piperonal present more amine (6.00 g) was added again. After stirring the reaction mixture for another 24 h at room temperature the imine was isolated. The reaction mixture was diluted with water (300 mL) and the organic layer was washed with water 200 mL*2, brine (200 mL) dried Na2SO4 and concentrated to provide the pure imine as a yellow oil (15.80 g, 100%). 1H NMR (300 MHz, CDCl3) delta 8.13 (s, 1H), 7.33 (s, 1H), 7.07 (d, J=8.10 Hz, 1H), 6.78 (d, J=8.10 Hz, 1H), 5.96 (s, 2H), 4.62 (t, J=5.4 Hz, 1H), 3.70 (d, J=4.2, 2H), 3.83 (s, 6H).

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, 2,2-Dimethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cushman, Mark S.; Ioanoviciu, Alexandra S.; Pommier, Yves G.; US2008/242692; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem