Category: ethers-buliding-blocks

19056-41-8, The chemical industry reduces the impact on the environment during synthesis 19056-41-8, name is 3-Bromo-4-methoxyaniline, I believe this compound will play a more active role in future production and life.

A flask containing compound QQ (0.966 g, 1.48 mmol), 4-amino-2-bromoanisole (0.35 g, 1.78 mmol), tris(dibenzylidineacetone)dipalladium(0) (0.068 g, 0.074 mmol), BINAP (0.092 g, 0.148 mmol), and sodium tert-butoxide (0.569 g, 5.92 mmol) was flushed with nitrogen, and then anhydrous o-xylene (30 mL) was added. The mixture was heated at 115 C. in an oil bath for two hours. At this time, the reaction was cooled to room temperature and the solvent was removed under reduced pressure. The brownish residue was redissolved in dichloromethane and filtered through a bed of celite. The filtrate was concentrated to dryness under reduced pressure, dissolved in THF (20 mL) and purged with nitrogen. Tetrabutylammonium fluoride (1.0 N in THF, 4.5 mL, 4.5 mmol) was added and the solution was stirred for 18 hours at room temperature. The solvent was removed under reduced pressure, and the residue partitioned between water and DCM. The organic layer was washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (1-10% MeOH in DCM) to give compound RR.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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6770-38-3, The chemical industry reduces the impact on the environment during synthesis 6770-38-3, name is 1,4-Bis(methoxymethyl)benzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 19 The procedure of Example 9 was repeated, except that 1 mmol of 1,4-bis(methoxymethyl)benzene was used instead of 4-methoxymethyltoluene to give terephthalaldehyde (yield: 53%) and 4-methoxymethylbenzaldehyde (yield: 20%) at a conversion rate from 1,4-bis(methoxymethyl)benzene of 96%.

The chemical industry reduces the impact on the environment during synthesis 1,4-Bis(methoxymethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daicel Chemical Industries, Ltd.; US6201156; (2001); B1;,
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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. 21702-84-1 name is 2,4-Dibromo-1-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. 21702-84-1

General procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether-ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC-MS analysis). The purity of the recovered MeOH was measured as more than 99 % by GC, and the water content of the recovered MeOH was measured as less than 0.12 % by use of the Karl Fischer method.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dibromo-1-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Guo, Ying; Ji, Si-Zhe; Chen, Cheng; Liu, Hong-Wei; Zhao, Jian-Hong; Zheng, Yu-Lin; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 41; 11; (2015); p. 8651 – 8664;,
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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 60792-79-2 as follows. 60792-79-2

Example 3 Preparation of 2-hydroxy-N-(2-(2-(2-((2Z,5Z,8Z,11Z,14Z,17Z)-eicosa-2,5,8,11,14,17-hexaenylthio)acetamido)ethoxy)ethyl)benzamide (1-1) In a typical run, sodium hydroxide (400 mg, 10 mmol) is dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) is added. The resulting reaction mixture is stirred at room temperature for 30 min. A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) is then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture is stirred at room temperature for 18 h and then concentrated under reduced pressure. The resulting residue is taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).

According to the analysis of related databases, 60792-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82120; (2011); A1;,
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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, 1535-73-5

Ethyl 6-((3-(trifluoromethoxy)phenyl)carbamoyl)nicotinate (5.5.2)To a stirring solution of 5-(ethoxycarbonyl)picolinic acid (0.50 g, 2.56 mmol) in DMF (10 ml) was added CDI (0.623 g, 3.84 mmol). The reaction was allowed to stir for 10 min and the 3-(trifluoromethoxy)aniline (0.41 ml, 3.07 mmol) was added. The solution was stirred overnight at room temperature. An LC-MS was obtained which indicated the presence of the product. Water was added to the reaction and the white precipitate was filtered. LC- MS of the solid confirmed the product as ethyl 6-((3- (trifluoromethoxy)phenyl)carbamoyl)nicotinate (0.45 g, 50 percent). 1 H NMR (400MHz CDCI3) deltaEta ppm 1 .36 (t, 3H), 4.39 (q, 2H), 7.13 (d, 1 H), 7.50 (t, 1 H), 7.94 (d, 1 H), 8.09 (s, 1 H), 8.29 (d, 1 H), 8.44 (d, 1 H), 9.19 (s, 1 H), 1 1 .1 1 (s, 1 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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ITHEMBA PHARMACEUTICALS (PROPRIETARY) LIMITED; MUSONDA, Chitalu, Christopher; EDLIN, Christopher, David; BOYLE, Grant, Alexander; WO2013/72903; (2013); A1;,
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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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., 22236-10-8

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l).

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; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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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. 41406-00-2, name is 3-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 41406-00-2

EXAMPLE 178 4-(3-Isopropoxyanilino)-6-methyl-2-(2-pyridinyl)pyrimidine The title compound was prepared from 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (82.3 mg, 0.4 mmol) and 3-isopropoxyaniline (60.4 mg, 0.4 mmol) similar to Example 173 and was isolated as a white solid (88 mg, 69%). 1H NMR (CDCl3): 8.64 (d, J=4.2 Hz, 1H), 8.35 (d, J=8.1 Hz, 1H), 7.7 (t, J=8.1 Hz, 1H), 7.24 (m, 1H), 7.15 (m, 1H), 6.96 (s, 1H), 6.76 (m, 2H), 6.60 (d, J=8.1 Hz, 1H), 6.18 (m, 1H), 4.45 (m, 1H), 2.37 (s, 3H), 1.25 (d, J=6.0 Hz, 6H).

The synthetic route of 41406-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. 111-95-5

To the product from step 2 (1.00 g, 5.29 mmol) in ACN (20 mL) was added bis(2-methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 C. for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCl3) delta 7.47 (bs, 2H), 3.77 (t, J=5.7 Hz, 4H), 3.52 (t, J=5.4 Hz, 4H), 3.25 (s, 6H). 13C NMR (75 MHz, CDCl3) delta 154.7 (s), 152.0 (s), 120.9 (s), 119.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t).

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 111-95-5.

Reference:
Patent; MediBeacon Inc.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (52 pag.)US2019/125902; (2019); A1;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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. 1462-37-9

After flushing the interior of the vessel with nitrogen, under nitrogen, 8.41 g (210 mmol) of sodium hydride (oily) and 80 ml of dry tetrahydrofuran were added to a 1000 ml four-necked flask, and while cooling with an ice-water bath, 34.00 g (100 mmol) in 350 ml of tetrahydrofuran was added dropwise. Immediately after the dropwise addition of DCMI in tetrahydrofuran solution, bubbles that appeared to be H 2 were observed. After foaming subsided, the temperature was raised to room temperature and stirred for 1 hour. Thereafter, while cooling the flask again with an ice-water bath, a solution of 50.01 g (233 mmol) of benzyl-2-bromoethyl ether dissolved in 50 ml of dry THF was added dropwise. After the dropwise addition, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes, then heated to 60 to 70 ¡ã C. and stirred for 18 hours. On the way, heating was stopped when benzyl-2-bromoethyl ether became a trace amount and consumption ceased almost at a time-dependent change by TLC.As a post-treatment, the flask was cooled with ice with stirring under nitrogen, 150 ml of ethyl acetate was added to the flask, then 100 ml of water was slowly added dropwise, the aqueous phase was separated off and the organic phase was washed with 100 ml of water For 2 times. The organic phase was concentrated with an evaporator to obtain 68.10 g of a viscous liquid with a yellowish tinge. Thereafter, silica gel column purification was carried out using a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 10/1 to 1/1 (volume ratio)), and the solvent was distilled off under reduced pressure to give the following compound 6 46.36 g (76.2 mmol: yield 76.2percent) was obtained as a viscous liquid.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; Machine: Mitsubishi ChemicalsCo ., Ltd .; Imai Nao Akira; Saito Yasuyo; Kawakami Kotoku; Fuji Tsuu Akira; (94 pag.)JP2017/222625; (2017); A;,
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The chemical industry reduces the impact on the environment during synthesis 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, I believe this compound will play a more active role in future production and life. 14869-41-1

To a suspension of compound 26-5 (0 1 g) and 2-chloroethoxy acetic acid (45 4 mg) m DMF (2 mL), was added4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholmium chloride (DMT-MM, 87 7 mg) The reaction mixture was stirred at room temperature overnight Then, according to the Step 29-1 in synthetic method for EXAMPLE 29, cychzation reaction was pursued to obtain compound 30-1 (90 mg) as a colorless amorphous solid

The chemical industry reduces the impact on the environment during synthesis 14869-41-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SCHERING CORPORATION; NISHIDA, Hidemitsu; SAITOH, Fumihiko; HIRABAYASHI, Tomokazu; CHACKALAMANNIL, Samuel; CHAN, Tin-Yau; CHELLIAH, Mariappan, V.; CLASBY, Martin, C.; DWYER, Michael, P.; GREENLEE, William, J.; XIA, Yan; WO2010/65717; (2010); A1;,
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