Category: ethers-buliding-blocks

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. Computed Properties of C9H11BrO

Step 2 To an acetonitrile (250 mL) solution of crude product 2 (24.5 g) obtained from Step 1, benzyl-2-bromoethylether A (27.3 mL, 173 mmol) and potassium carbonate (27.5 g, 199 mmol) were added, under nitrogen atmosphere, followed by heating at reflux for 4 hours and a half. The reaction solution was filtered and then the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate and concentrated in vacuo to yield crude product 3 (54.6 g). LC/MS (Method A): 1.97 min, [M+H]+ = 319.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi&Co., Ltd.; EP2327704; (2011); A1;,
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Reference of 5467-58-3, These common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, 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.

Under a nitrogen atmosphere,Add 1-bromo-4-methoxynaphthalene (42.4 mg, 0.18 mmol) to a 25 mL sealed tube.Dichloroethane 2.0 mL, N-trifluoromethoxy-2,6-dichloropyridine hexafluoroantimonate (101 mg, 0.22 mmol) was added at 80 C for 36 hours. After adding 1.0 mL of a saturated aqueous solution of sodium hydrogencarbonate and 8.0 mL of distilled water, it was extracted with dichloromethane (15 mL ¡Á 3), washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Filter and spin dry the solvent. Column chromatography gave 18.0 mg of 1-bromo-2-trifluoromethoxy-4-methoxynaphthalene in a yield of 31%. 10.8 mg of 1-bromo-3-trifluoromethoxy-4-Methoxynaphthalene, yield 19%. The total yield is 50%.

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Mei Benzhaoxiong; Zhou Min; Hu Jinbo; (18 pag.)CN105017143; (2018); B;,
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Application of 41789-95-1, The chemical industry reduces the impact on the environment during synthesis 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

General procedure: An amine (1 mmol, 2 equiv) was added to a solution of Nchlorosuccinimide(149 mg, 1.1 mmol, 2.2 equiv) in CH2Cl2(5 mL) at r.t. in the dark. After 3 h, Ir(dtbpy)(ppy)2PF6 (4 mg,5 mumol, 0.01 equiv), Ph3N (245 mg, 1 mmol, 2 equiv), andbenzoxazole (60 mg, 0.5 mmol, 1 equiv) were added. Thereaction rube was sealed and placed at a distance of 5 cm from 3 W blue LED and stirred for 60 h. After the reactionwas complete, the solvent was evaporated under vacuo. Thecrude mixture was purified by flash column chromatographyeluting with a mixture of PE-EtOAc

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Jia-Di; Liu, Yu-Xia; Xue, Dong; Wang, Chao; Xiao, Jianliang; Synlett; vol. 25; 14; (2014); p. 2013 – 2018;,
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Electric Literature of 74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-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.

To a solution of 20b (60 g, 0.2256 mol) and anhydrous Et2O (1 L)cooled to -78¡ã C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78¡ã C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78¡ã C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30¡ã C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10¡ã C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5percent EtOAc) to afford 21.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/88015; (2007); A1;,
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Synthetic Route of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: At 0 C, a solution of 3(4)-bromobenzoyl chloride or 5-bromothiophene-2-carbonyl chloride (1 eq) in CH2Cl2 (2 ml/eq) was added drop wise to a solution of N-methylbenzylamine (1 eq) and triethylamine (1.15 eq) in CH2Cl2 (2 ml/eq). The mixture was kept stirred at 0 C for 3 h and evaporated under reduced pressure. The residue was purified by FC with n-hexane/ethyl acetate as eluant.

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Kuiying; Al-Soud, Yaseen A.; Wetzel, Marie; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5978 – 5990;,
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Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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: 3401-47-6

Under argon, in a flame-dried vessel, a solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36) in THF (50 ml) was added dropwise to the magnesium (0.905 g, 37.2 mmol) in THF (15 ml). The reaction mixture was stirred at room temperature for 2 h then at 50C for 1h. It was then cooled to -78C and trimethylborate (11.4 ml, 101.7 mmol) was slowly added. After 2 h at -78C, the mixture was allowed to warm to room temperature and stirred overnight. After addition of water (40 ml), THF was removed under reduced pressure. The mixture was extracted with dichloromethane; the combined organic phases were dried over MgSO4, filtered and concentrated. Recrystallization from dichloromethane gave the boronic acid as a white powder (80% yield). 1H NMR (400.14 MHz, CDCl3): d = 4.08 (s, 3H), 6.22 (s, 2 H), 7.28 (d, J = 9.1 Hz, 1H), 7.34-7.43 (m, 1H), 7.47-7.56 (m, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.9 Hz, 1H), 8.86 ppm (d, J = 9.1 Hz, 1H); 13C{1H} NMR (75.47 MHz, [D6]DMSO): d = 56.1, 113.7, 121.8, 122.7, 125.8, 127.4, 127.8, 128.5, 129.4, 135.6, 159.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.

Reference:
Article; Castillo, Angelica Balanta; Perandones, Bernabe F.; Zangrando, Ennio; Gladiali, Serafino; Godard, Cyril; Claver, Carmen; Journal of Organometallic Chemistry; vol. 743; (2013); p. 31 – 36;,
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Related Products of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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: To a solution of 4-bromo-2-methoxyaniline (11a) (300 mg, 1.48 mmol) in anhydrous CH2Cl2(15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under an argon atmosphere.The mixture was stirred at room temperature for 16 h.After being quenched with 1 N HCl(aq) (1.0 mL), water and CH2Cl2were added and then the layers were separated. The combinedorganic phases were washed with brine, dried over anhydrousNa2SO4, filtered and concentrated. The residue was purified bycolumn chromatography on silica gel (EtOAc/hexane, 10:90 to15:85) to give 13a (490.1 mg, 99%) as a light yellow oil.

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:
Article; Bufton, Joshua C.; Bullock, Alex N.; Cuny, Gregory D.; Dai, Bing; Degterev, Alexei; Duddupudi, Anantha Lakshmi; Gyrd-Hansen, Mads; Hu, Ming; Li, Li; Pinkas, Daniel M.; Schlicher, Lisa; Suebsuwong, Chalada; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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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. 109-85-3, name is 2-Methoxyethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

EXAMPLE 532-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-1 -[2-(methyloxy)ethyl]-1 H-benzimidazole-6- carbonitrile hydrochlorideStep 1 . 5-bromo-N-[2-(methyloxy)ethyl]-2-nitroaniline: 4-bromo-2-fluoro-1 -nitrobenzene (0.3 g, 1.336 mmol), 2-(methyloxy)ethylamine (0.1 17 ml_, 1.336 mmol), and DIEA (0.238 ml_, 1 .336 mmol) in Ethanol (5 mL) were irradiated by microwave at 100C for 30 min. The reaction mixture was partitioned between dichloromethane and brine. The aqueous layer was extracted with DCM twice. The combined DCM layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified via Biotage (SNAP Cartridge KP Sil 25 g, 0-10% EtOAc/Hexane) to yield 5-bromo-N-[2-(methyloxy)ethyl]-2-nitroaniline (0.374 g, 1.286 mmol, 96 % yield). 1H NMR (400 MHz, CDCI3) delta 8.22 (br. s., 1 H), 8.04 (d, J = 9.1 Hz, 1 H), 7.05 (d, J = 1.5 Hz, 1 H), 6.78 (dd, 1 H), 3.69 (t, 2 H), 3.48 (t, 2 H), 3.45 (s, 3 H); MS (m/z) 275.1 (M+H)+.

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; GLAXO GROUP LIMITED; BODMER, Vera, Q.; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; KING, Bryan, W.; LAKDAWALA SHAH, Ami; LEISTER, Lara, Kathryn; WANG, Gren, Z.; WISNOSKI, David, Duff; HARRIS, Philip, A.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; WILSON, Matthew, A.; WO2011/123609; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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 53087-13-1, HPLC of Formula: C13H11BrO

Example 66; 2-[4-[2-[5-[2-[2-benzyloxy-4-[butyl(4-hydroxybutyl)amino]phenyl]vinyl]thiophene-2-yl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile(66-1) 4-[(3-benzyloxyphenyl)butylamino]-1-butanol In 75 ml of dioxane were dissolved 5.19 g (19.7 mmol) of 3-benzyloxybromobenzene and 3.72 g (25.6 mmol) of 4-butylamino-1-butanol. To this mixture was added 5.89 g (29.5 mmol) of potassium hexamethyldisilazide and the mixture was stirred with heating at 100 C. for 22 hours. After the reaction mixture was poured into 200 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.22 g of a light brown oily matter (yield: 34.4%). 1H-NMR (600 MHz, CDCl3) delta: 0.93 (3H, t, J=7.7 Hz), 1.29-1.35 (2H, m), 1.51-1.66 (6H, m), 3.22 (2H, t, J=7.7 Hz), 3.26 (2H, t, J=7.7 Hz), 3.66 (2H, t, J=6.9 Hz), 5.05 (2H, s), 6.27-6.31 (3H, m), 7.11 (1H, t, J=8.2 Hz), 7.30-7.33 (1H, m), 7.37-7.39 (2H, m), 7.43-7.45 (2H, m)

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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otomo, Akira; Aoki, Isao; Miki, Hideki; Tazawa, Hidehisa; Yokoyama, Shiyoshi; US2012/172599; (2012); A1;,
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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. 2252-44-0, name is 3-(Trifluoromethoxy)bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H4BrF3O

The title compound was prepared in the manner analogous to Example 3A using 3-hydroxymethylphenylboronic acid and 1-bromo-3-trifluoromethoxy-benzene. MS m/z 251 (M-1).

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 2252-44-0.

Reference:
Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); A1;,
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