Ethers-buliding-blocks

Reference of 1535-73-5, The chemical industry reduces the impact on the environment during synthesis 1535-73-5, name is 3-Trifluoromethoxyaniline, I believe this compound will play a more active role in future production and life.

Add 3-(trifluoromethoxy)aniline (1.0 g, 5.65 mmol), pyridine (0.89 g, 11.3 mmol) to DCM (20 mL) and cool to 0 C. Add dropwise phenyl chloroformate (1.15 g, 7.34 mmol). After addition, stir for 1 hr. TLC (PE:EtOAc=3:1) shows the reaction is complete. Add water to the mixture, extract with DCM (10 mL*3), combine the organic layer, wash with 1N HCl solution, brine sequentially, and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the product (1.50 g, 89%). Intermediates D42-D46 can be synthesized with similar method (Table D9)

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; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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. Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

General procedure: Corresponding 3-bromopropoxyaryl (5 mmol, 1 equiv) and amines(7.5 mmol, 1.5 equiv) was dissolved in 30 mL CH3CN. The reaction was purged with argon 3 times and stirred at reflux for 5 h, and then the mixture was cooled to room temperature and added AcOEt. Afte rwashing with brine 3 times, the organic layer was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. Purification of the crude residue by column chromatography on silica gel afforded target compounds.

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

Reference:
Article; Chang, Qi; Chen, Zhuo; Hu, Gaoyun; Hu, Liqing; Li, Qianbin; Long, Jing; Bioorganic and medicinal chemistry; vol. 28; 9; (2020);,
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Application of 156573-09-0, These common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, 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.

Seventh Step: 1.76 g of well dried magnesium and 10 mL of THF were placed in a reactor under nitrogen atmosphere, and heated to 53 C. 17.2 g of the compound (1) dissolved in 30 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 56 C., followed by stirring for 30 minutes. Thereafter, 6.0 g of the compound (16) dissolved in 10 mL of THF was slowly added dropwise thereto at a temperature range of from 50 to 55 C., followed by stirring for 30 minutes. After cooling the resulting reaction mixture to 25 C., the reaction mixture was poured into and mixed with a mixture of 100 mL of 1N hydrochloric acid and 100 mL of toluene. The mixture was then separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution, and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain 18.5 g of 1-(4-ethoxy-2,3-difluorophenyl)-4-vinylcyclohexanol (17) as a yellow liquid.

The synthetic route of 156573-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHISSO Corporation; CHISSO PETROCHEMICAL Corporation; US2008/63814; (2008); A1;,
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Electric Literature of 446-59-3, 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. 446-59-3 name is 2-Bromo-1-fluoro-3-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.

A mixture of 2-bromo-3-fluoroanisole (25 g), hexamethylenetetramine (34.2 g), and trifluoroacetic acid (150 mL) was stirred at 90C for 27 hours. The reaction mixture was allowed to cool to room temperature, and then 1 M hydrochloric acid was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, and then the organic layer was concentrated to about half of its volume. To the concentrated organic layer was added aqueous sodium hydroxide, and then the organic layer was separated from the mixture and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and filtrated, and the solvent was removed. The obtained crude product was purified by silica gel column chromatography (heptane : ethyl acetate = 94 : 6 to 73 : 27) to afford the title compound as a white solid (22.3 g).1H-NMR (CDCl3) delta: 4.01 (3H, s), 6.82 (1H, d, J = 8.8 Hz), 7.85 (1H, dd, J = 8.8, 7.7 Hz), 10.22 (1H, d, J = 0.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-fluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KATOH, Takahiro; IIDA, Masatoshi; TERAUCHI, Yuki; YAMAGUCHI, Kazuya; HIROSE, Toshiyuki; YOKOYAMA, Fumiharu; NISHIMORI, Hikaru; OBUCHI, Yutaka; NABESHIMA, Hiroshi; TAKAKI, Emiri; (250 pag.)WO2017/150654; (2017); 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H5BrF3NO

Step 2: 5-methyl-2-(trifluoromethoxy) aniline 5-bromo-2-(trifluoromethoxy) aniline (1.14g, 4.46mmol) obtained from the last step, methyl boronic acid (0.72g, 12mmol), potassium carbonate (1.66g, 12mmmol), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (0.29g, 0.4mmol) and 1,4-dioxane (25mL) were added to a 100mL reaction flask. The reaction mixture was heated up to 80 C and stirred overnight. After completion of the reaction, the reaction solution was concentrated and dissolved in ethyl acetate. The organic phase was washed with saturated ammonium chloride and saturated brine, dried, concentrated and purified by column chromatography (ethyl acetate/petroleum ether=1:15) to obtain the title compound (yellow oil, 0.61g, 72%). (MS: [M+1] 192.1)

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Pearl Biotechnology Limited Liability Company; DONG, Jiaqiang; ZHONG, Boyu; YUAN, Hongbin; SHI, Quan; CHU, Shaosong; ZHANG, Deyi; ZHANG, Ruihao; (219 pag.)EP3150592; (2017); A1;,
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Electric Literature of 768-70-7,Some common heterocyclic compound, 768-70-7, name is 3-Ethynylanisole, molecular formula is C9H8O, 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 consisting of 2-(3-iodo-4-methoxybenzoyl)isoindoline (50 mg, 0.132 mmol), 3- ethynylanisole (52 mg, 0.396 mmol), CuI (5 mg, 0.026 mmol), Pd(PPh3J2CI2 (18 mg, 0.026) and TEA (0.055 ml_, 0.396 mmol) in 7.5 ml. of toluene was stirred under nitrogen overnight in a 40 ml_ vial at 1000C. Upon cooling to rt, the crude mixture was filtered through a plug of silica gel and washed through with EtOAc. The solvents were then removed under reduced pressure and the residue was purified by flash chromatography on silica gel (20:1 CH2CI2/Me0H) to afford 35 mg (69%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCI3): consistent; MS (ES+) mlz 384.1 (M+H).

The synthetic route of 768-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); 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 1758-46-9 as follows. Recommanded Product: 1758-46-9

d) (6-Chloro-4-methyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 6-Chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (106 mg, 0.30 mmol) and 2-phenoxyethyl amine (168 mg, 1.2 mmol) were dissolved in acetonitrile (0.9 ml) and heated to 170¡ã C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, the solvent was evaporated and the residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1) to yield the title compound as a white solid (88 mg, 93percent). (MS: m/e=316.0, 318.0 [M+H+]). 1H NMR (CDCl3): delta 1.23 (3H, d), 3.56 (2H, m), 4.05 (2H, t), 4.47 (1H, q), 5.95 (1H, bs), 6.27 (1H, bs), 6.69 (1H, d), 6.90-7.01 (4H, m), 7.29 (2H, t).

According to the analysis of related databases, 1758-46-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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Related Products of 6298-96-0, 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. 6298-96-0 name is 1-(4-Methoxyphenyl)ethylamine, 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.

A solution of (S)-(-)-1-(4-methoxyphenyl)ethylamine (25.0 g, 166 mmol) and 6,7-dihydro-8(5f/)-quinolinone (24.0 g, 166 mmol, J. Org. Chem., 2002, 67, 2197-2205) in dichloromethane was treated with glacial acetic acid (14.0 mL, 249 mmol) and sodium triacetoxyborohydride (53.0 g, 249 mmol). The reaction mixture was stirred at room temperature for 15 hours and then treated with sodium carbonate (106 g, 996 mmol) dissolved in water. The resulting mixture was stirred for 30 minutes and then diluted with dichloromethane. The phases were separated and the aqueous solution extracted with an additional portion of dichloromethane. The combined organic solutions were dried over MgSO4 and concentrated to dryness at reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution of dichloromethane to 97:3 dichloromethane/2M ammonia in MeOH) followed by recrystallization from hexane to afford 33 g (70%) of (8S)-Lambda/-{(1 S)-1-[4-(methyloxy)phenyl]ethyl}-5,6,7,8-tetrahydro-8- quinolinamine as a white crystalline solid. 1H NMR (CDCI3): delta 8.40 (m, 1 H), 7.33 (m, 3H), 7.04 (m, 1 H), 6.84 (d, 2H), 4.02 (m, 1 H), 3.83-3.78 (m, 4H), 2.73-2.62 (m, 2H), 1.82 (m, 1H), 1.72 (m, 1 H), 1.57 (m, 2H), 1.43 (d, 3H).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; SVOLTO, Angilique, Christina; WO2007/87548; (2007); A2;,
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Synthetic Route of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The nitro ether (149 mmol) was dissolved in ethanol (37.5 mL), diluted with water (25 mL), and was treated with ammonium chloride (84.7 mmol) and iron powder EPO (105 mmol). The reaction mixture was heated at reflux for 30 minutes and the suspension was filtered through Celite. The filter cake was washed with ethanol three times and the combined filtrates were concentrated. The residue was dissolved in water and .the pH adjusted to 9-10 with 5 M sodium hydroxide. The aqueous layer was extracted with ethyl acetate (3xl00mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to a yellow oil. The oil was dissolved in acetic anhydride (23.5 mmol) and the reaction mixture was maintained at rt for 16 h. The reaction mixture was diluted with water (50 mL) and was neutralized with solid sodium bicarbonate. The precipitated solids were isolated by filtration, washed with water, and dried to provide the acetamide in 62% yield as a light yellow solid.

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

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/69097; (2006); A2;,
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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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6F3NO

. (2-Trifluoromethox -phenyl)-carbamic acid ethyl esterTo a solution of 2-(trifluoromethoxy)aniline (15.9 g, 0.09 mol) in DME (300 ml_) at -5 C (ice/salt bath) is added sodium hydride (3.6 g, 60% by weight, 0.09 mol) in portions. The suspension is warmed to r.t. and ethyl chloroformate (7.5 ml_, 0.08 mol) is added dropwise. The reaction mixture is stirred for 2 h at r.t. then heated to reflux for 1 .5 h. The mixture is then cooled to r.t. and water (150 ml_) is slowly added to quench the reaction. The phases are separated and the water layer is extracted with EtOAc (2×100 ml_). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/heptanes (1 -5%) as eluent to afford the title product (1 1 .0 g, 49%) as an amber oil. 1 H NMR (300 MHz, CDCI3) delta 8.20 (d, J = 8.1 Hz, 1 H), 7.30-7.22 (m, 2H), 7.07 (app t, 1 H), 6.90 (br s, 1 H), 4.25 (q, J = 7.2 Hz, 2H), 1 .34 (t, J = 7.2 Hz, 3H);19F NMR (300 MHz, CDCI3) delta -57.32 (s, 3F);LC Rt: 2.96 min; MS 250 (M+1 , 94%).

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 1535-75-7.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; LIANG, Guyan; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/79102; (2011); A1;,
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