Category: ethers-buliding-blocks

Reference of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

A solution of 3-fluoro-4-(trifluoromethoxy)aniline [CAS 101 7779-69-9] (32.0 g, 164 mmol) in CH3CN (600 mL) was stirred on an ice-bath. N-iodo-succinimide (40.59 g, 180.4 mmol) was added and the reaction mixture was allowed to slowly reachroom temperature while stirring overnight. The solvent was concentrated under reduced pressure. Water was added and the product was extracted with EtOAc (2x 300 mL). The combined organic layers were washed with and an aqueous solution of Na2S2O3 (500 mL), brine (500 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by columnchromatography on silica gel (eluent: petroleum ether/EtOAc gradient 50/1 to30/1). The desired fractions were combined and evaporated under reduced pressure to provide 5-fluoro-2-iodo-4-(trifluoromethoxy)aniline 7a (45 g).

The synthetic route of 1017779-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (91 pag.)WO2017/167950; (2017); A1;,
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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO2

c) 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylidene imidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide (example 53) [0196] HOBt (84 mg; 0.55 mmol; 1.5 eq), DIPEA (323 muL; 1.85 mmol; 5 eq) and 4-(2-methoxyethoxy)aniline (81 mg; 0.48 mmol; 1.3 eq) were added to a solution of 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (150 mg; 0.37 mmol; 1 eq) in dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 2 days. Ethyl acetate (10 mL) and water (5 mL) were added and the layers were separated. The organic layer was washed with saturated ammonium chloride (10 mL), water (10 mL) and sodium chloride (2 x 15 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was triturated in ethyl acetate, washed with petroleum ether, and concentrated to dryness. The residue was taken up in ethyl acetate/cyclohexane (200 muL) until precipitation, filtration. The title compound, 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide, was obtained in 25 % yield (50 mg) as a yellow solid. 1H-NMR (Acetone-d6): delta (ppm) 2.85 (m, 1H), 3.17 (m, 2H), 3.36 (s, 3H), 3.40 (m, 1H), 3.65 (m, 2H), 3.68 (s, 3H), 3.70 (m, 1H), 4.09 (m, 2H), 4.31 (m, 1H), 4.63 (m, 1H), 6.87 (m, 4H), 7.25 (m, 4H), 7.49 (m, 4H), 9.34 (s, 1H); MS (ESI+): m/z = 551.9 [M+H]+.

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 33311-29-4.

Reference:
Patent; Vivalis; Guedat, Philippe; Berecibar, Amaya; Ciapetti, Paola; Venkata Pithani ,Subhash; Trouche, Nathalie; EP2664616; (2013); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Safety of 1-(3-Methoxyphenyl)-N-methylmethanamine

Step B: Ethyl acrylate (33.0 mL, 298 mmol) was added to a stirred mixture of benzylamine (15.0 g, 99.2 mmol) from Step A above and acetic acid (3 mL) at 0 C. The mixture was heated at 80 C. for 4 hours and allowed to cool to room temperature before diluting with dichloromethane (300 mL). The reaction mixture was washed with saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo. The residue was treated with toluene and the resulting solution concentrated in vacuo in order to remove residual ethyl acrylate, affording the ester (25.0 g, 100%) as a colorless oil: 1H NMR (500 MHz, CDCl3) delta 7.22 (t, J=8.0 Hz, 1H), 6.89-6.86 (m, 2H), 6.78 (dd, J=8.2, 2.5 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.48 (s, 2H), 2.74 (t, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 2.21 (s, 3H), 1.25 (t, J=7.1 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 202865-59-6, name is 2-Bromo-4,6-difluoroanisole, 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 202865-59-6, Application In Synthesis of 2-Bromo-4,6-difluoroanisole

[00190] Intermediate 18A. l-(3,5-Difluoro-2-methoxyphenyl)-2- (diphenylmethylene)hydrazine: To a mixture of palladium (II) acetate (0.040 g, 0.18 mmol) and xantphos (0.104 g, 0.179 mmol) in toluene (1 mL), l-bromo-3,5-difluoro-2- methoxybenzene (4.0 g, 18 mmol), (diphenylmethylene)hydrazine (3.52 g, 17.9 mmol) and sodium tert-butoxide (2.41 g, 25.1 mmol) were added followed by the addition of toluene (4 mL). The mixture was degassed twice and stirred for 6 h at 100 C under argon. After cooling to room temperature, EtO Ac and water were added. The organic layer was separated. The aqueous layer was extracted one more time with EtOAc. The combined organics were washed with water and brine, dried over MgSC^, filtered, and concentrated. The crude was purified by flash chromatography, eluting with EtOAc/hexanes to give Intermediate 18A (6.0 g, 84% yield). LCMS (ESI) m/z 339.4 (M+H)+, RT = 2.33 min (Method D). NMR (400 MHz, CDC13) delta ppm 3.63 (br. s, 3 H), 6.14 – 6.38 (m, 1 H), 7.08 – 7.20 (m, 5 H), 7.45 – 7.68 (m, 5 H), 7.97 (s, 1 H). 19F NMR (376.5 MHz, acetone-d6) delta ppm -115.46, -129.88.

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-Bromo-4,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.67 g (5 mmol) 4-[({[(1R, 2S, 4R)-1, 7, 7-TRIMETHYLBICYCLO [2.2. 1] hept-2-yl] amino} carbonyl)- AMINO]-LH-PYRROL-2-CARBONSUREETHYLESTER (Beispiel 1) werden IN 10 ml absolutem DMF gelst und mit 1.07 g (9.5 mmol) Kalium-tert-butylat versetzt. Nach 5 min Rhren bei RT werden 1.91 g (9.5 mmol) 1-BROMETHYL-2-PHENYLETHER zugegeben. Die Reaktionsmischung wird ber Nacht bei RT gerhrt, dann werden noch einmal 600 mg (3 mmol) 1-BROMETHYL-2-PHENYLETHER und 336 mg (3mmol) KALIUM-TERT-BUTYLAT zugegeben. Die Reaktionsmischung wird ber Nacht bei RT gerhrt, dann werden langsam 3.5 ml Wasser und 0.5 ml Methanol zugetropft. Die entstehenden Kristalle werden abgesaugt und mit Wasser/Methanol (1 : 1-Gemisch) und wenig Methanol gewaschen. Ausbeute : 1. 87 g (83 percent d. Th.) MS (ESI+) : m/z = 454 (M+H) + 1H-NMR (300MHZ, DMSO-d6) : deltaelta; = 7.9 (s, 1H), 7.25 (TR, 2H), 7.2 (d, lH), 6.85-6. 95 (m, 3H), 6.65 (d, 1H), 6.0 (d, 1H), 4.6 (TR, 2H), 4.15-4. 25 (m, 4H), 3.95 (m, 1H), 2.2 (M, 1H), 1.55-1. 8 (m, 3H), 1.35-1. 1 (m, 2H), 1.25 (tr, 3H), 0.9 (s, 3H), 0.85 (s, 3H), 0.8 (D, 1H), 0.75 (s, 3H) ppm.

The synthetic route of ((2-Bromoethoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/52852; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-2-methoxynaphthalene

1-Bromo-2-methoxynaphthalene (20.0 g, 84.4 mmol),Phenylboronic acid (11.3 g, 92.8 mmol),Palladium acetate (0.10 g, 0.46 mmol),Triphenylphosphine (0.85 g, 2.78 mmol)And potassium phosphate (40.9 g, 177.9 mmol) were placed in a flask,Add 60 ml of water and 120 ml of dimethoxyethane mixed solution and reflux for 6 hours. After cooling at room temperature,Ammonium chloride aqueous solution (150 mL)And 200 mL of diethyl ether were injected,The organic layer was separated and the residue was extracted with diethyl ether,After drying the collected organic layer with magnesium sulfate,After removal of volatiles,The residue was purified with hexane using a silica gel chromatography tube,13.0 g (yield: 66%) of 2-methoxy-1-phenylnaphthalene as a colorless liquid was obtained.

The synthetic route of 3401-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK INNOVATION COMPANY LIMITED; OK, MYUNGAHN; SHIN, DONGCHEOL; JEONG, JISU; HAHN, JONGSOK; LEE, HOSEONG; SHIN, DAEHO; (23 pag.)JP5656843; (2015); B2;,
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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H16O4

Another exemplary study was carried out as follow: Compound J and AcOH (7.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C . Tetramethoxypropane (1.01 equivalents) was charged to the reactor and the j acket was set to maintain an internal temperature of 95 C. Once at temperature, the reaction continued mixing for 1.5 hours and then an IPC sample was taken. The passing criteria for this IPC was 60 C to prevent premature precipitation. Once the target volume was reached the jacket was set to maintain an internal temperature of 50 C. A 4 M solution of NaOH was then charged to the reactor via cannula to neutralize the remaining AcOH. This typically required approximately 10 volumes of the base solution. The neutralization was monitored by pH probe. Solids began to precipitate during the course of the charge. Once neutralized, the slurry was cooled to 20 C and held at that temperature for 1 hour prior to isolation via Buchner funnel. The cake was washed twice with 2 volumes of water and once with 2 volumes of MeOH. The solids were then dried to constant weight in a vacuum oven to provide Compound H. This procedure had been performed on 110 g scale to produce a granular light brown solid.

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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: 32338-02-6

Under inert gas protection, 100 ml of a mixed organic solvent of acetic acid and acetonitrile with a volume ratio of 2: 1 was added to the reactorAgent, 10mmol successively added thereto the above formula (I-1) compound of the formula 12mmol (II-1) compounds, 1 mmol of copper trifluoromethanesulfonate catalyst, 1 mmol of cocatalyst, 20mmol bis (trifluoroacetate) iodobenzene, and To the reaction solution was added 15 mmol of isoamyl nitrite. The temperature was raised to 50 ¡ã C with stirring, and the reaction was stirred at this temperature for 8 hours. After the reaction was completed, all volatiles were removed in vacuo and the product extracted with ethyl acetate, the organic solvent phase was removed and the resulting residue was separated by column chromatography on 300-400 mesh silica gel, elution solvent is a volume ratio of 4: 1 petroleum ether and acetic acid Ethyl ester, the compound of the above formula (III-1) was obtained in a yield of 93.5percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32338-02-6, its application will become more common.

Reference:
Patent; Zhou Xiaofang; (6 pag.)CN107056703; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 109-85-3,Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, 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 2,3-dichloro-1,4-naphthoquinone (0.341g, 1.50mmol) in 1.5mlof ethanol was added 2-methoxyethylamine (0.124g, 1.65mmol) and triethylamine (0.227g,2.25mmol) and the mixture stirred at r. t. for 18h. The red precipitate formedwas filtered under suction, washed with distilled water and dried to afford (4) as a dark red solid, 87.8%.1H (CDCl3) delta 8.15 (dd, 1H, J=0.94, 7.68Hz), 8.03 (dd, 1H, J=0.99, 7.67Hz), 7.72 (dt, 1H, J=1.31, 7.59Hz), 7.62 (dt, 1H, J=1.28, 7.55Hz), 6.36 (br s, 1H), 4.06(dd, 2H, J=5.60, 10.62Hz), 3.63(t, 2H, J=5.17Hz), 3.42 (s, 3H); 13C(CDCl3) delta 180.42, 176.84, 144.37, 134.85, 132.67, 132.44, 129.88,126.80, 77.20, 71.22, 58.95, 44.50.

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

Reference:
Article; Ho, Si-Han Sherman; Sim, Mei-Yi; Yee, Wei-Loong Sherman; Yang, Tianming; Yuen, Shyi-Peng John; Go, Mei-Lin; European Journal of Medicinal Chemistry; vol. 104; (2015); p. 42 – 56;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 solution of 6.00 g (22.8 mmol) of 1,2-dibromo-4,5-dimethylbenzene in 12 mL of tetrahydrofuran wasadded to preliminary prepared 30 mL of a 1M solutionof iso-PrMgLiCl in tetrahydrofuran and stirred at -17to -13C. After 3 h, 5.12 g (23.25 mmol) of chlorodiphenylphosphinewas added dropwise to the solutionat -20 to -10C. The obtained solution was stirred for30 min at -10C, and then it was allowed to warm upto room temperature, stirred for additional 16 h, andevaporated. 30 mL of methylene chloride and 20 mLof a saturated aqueous solution of ammonium chloridewere added to the residue. The organic phase wasseparated and dried over anhydrous sodium sulfate.The residue after the evaporation was recrystallizedusing an ethanol-acetone mixture.

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-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem