Category: ethers-buliding-blocks

Electric Literature of 17715-69-4, 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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A suspension of Pd2(dba)3 (6.9 mg, 0.0075 mmol), tBu3PHBF4 (8.7 mg,0.03 mmol), KOH (42 mg, 0.75 mmol), aryl bromide 9 (0.36 mmol) and tetralone 10(0.3 mmol) in a mixture of dioxane/water (4:1, v/v, 3 mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100 °C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4,filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Manvar, Dinesh; Fernandes, Talita De A.; Domingos, Jorge L.O.; Baljinnyam, Erdenechimeg; Basu, Amartya; Junior, Eurides F.T.; Costa, Paulo R.R.; Kaushik-Basu, Neerja; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 51 – 54;,
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Adding a certain compound to certain chemical reactions, such as: 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, 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 156573-09-0, category: ethers-buliding-blocks

Under a nitrogen atmosphere,60 g of trimethylsilylacetylene,120 g of 4-ethoxy-2,3-difluorobromobenzene, 1.9 g of copper iodide,11.7 g of tetrakistriphenylphosphine palladium were dissolved in 500 mL of DMF,And the mixture was stirred at 70 C. for 2 hours.To the reaction mixture were added toluene,Add water,After stirring, the organic layer was separated.The organic layer was washed with waterwater,Ammonia water,Followed by washing with saturated saline in this order,After drying with anhydrous sodium sulfate,The solvent was distilled off under reduced pressure.The obtained crystalRecrystallization and purification by column chromatography (silica gel)120 g of trimethyl- (4-ethoxy-2,3-difluorophenylethynyl) silane was obtained.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DIC CORPORATION; NOSE, SAYAKA; SAITOU, YOSHITAKA; KADOMOTO, YUTAKA; (18 pag.)JP5696874; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, 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 62415-74-1, Product Details of 62415-74-1

General procedure: Into a dried two-necked flask (50 mL) equipped with a condenser were placed a stirrer bar, Mg powder (99.9%, 8 mmol), LiCl (8 mmol),DMI (10 mL), and chlorotrimethylsilane (16 mmol). After stirring the mixture at rt for 15 min, 1,2-dibromoarene (1 mmol) was added and the mixture was stirred for 4 h. The mixture was quenched with sat.NaHCO3 and the resulting precipitates were filtered off. The filtrate was extracted with hexane (3 ×) and the combined organic extracts were washed with brine, dried (anhyd Na2SO4), and concentrated by a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexane or hexane/CH2Cl2).

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, 1,2-Dibromo-4-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kitamura, Tsugio; Yamada, Rin; Gondo, Keisuke; Eguchi, Nobuo; Oyamada, Juzo; Synthesis; vol. 49; 11; (2017); p. 2495 – 2500;,
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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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7F2NO

4-(Difluoromethoxy)aniline (1 g, 6.28 mmol) was dissolved in aqueous hydrochloric acid (12%, 7.35 ml, 25.1 mmol). The solution was cooled to 0 C. and sodium nitrite (434 mg, 6.28 mmol) dissolved in water (2 ml) was slowly added at a temperature below 5 C. After being stirred at 0 C. for 30 min, a solution of ethyl isocyanoacetate (711 mg, 6.28 mmol) and sodium acetate (5.16 g, 62.8 mmol) in MeOH (20 ml) and water (6 ml) was slowly added dropwise at the same temperature. The reaction mixture was stirred for 2 h at 0 C. The solvent was evaporated, 1 M hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was washed with sodium bicarbonate solution and brine and dried with MgSO4. After chromatography (Silica gel, 40 g, 50% EtOAc in heptane) 220 mg ester was obtained that was dissolved in a mixture of tetrahydrofuran (2 ml), methanol (1 ml) and water (1 ml). Lithium hydroxide hydrate (97.8 mg, 2.33 mmol) was added and the solution was heated to 80 C. for 2 h. The solvent was removed under reduced pressure. The residue obtained was dissolved in 1 M hydrochloric acid and the solution was extracted with ethyl acetate twice. The combined organic layers were dried over MgSO4 and evaporated. The orange solid was recrystallized in a mixture of heptane and ethyl acetate (4:1). 121 mg (7%) of an off-white solid was obtained. 1H NMR (300 MHz, CDCl3) ? ppm: 7.34 (t, 1H; J=73 Hz), 7.41 (d, 2H; J=8.7 Hz), 7.95 (d, 2H; J=8.7 Hz), 9.38 (s, 1H).

According to the analysis of related databases, 22236-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Galley, Guido; Ghellamallah, Cedric; Norcross, Roger; Pflieger, Philippe; US2015/191458; (2015); 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. 1758-46-9, name is 2-Phenoxyethylamine, A new synthetic method of this compound is introduced below., Computed Properties of C8H11NO

General procedure: A solution of 2-phenoxyethylamine (1.31 mL, 10 mmol) in methanol (10 mL) was added to a solution of triethylamine(Et3N) (2.76 mL, 20 mmol) in methanol (10 mL) at 0 C. A solution of 2-chloropyridine (3.80 mL, 40 mmol) in methanol(10 mL) was then added at 0 C under N2. After being stirred for 30 min, the reaction mixture was heated to 25 C and stirred for 3 days. Then, the solvent was evaporated under reduced pressure to afford a yellow solid L1 washed with methanol and dried under vacuum. Yield: 2.31 g (79%).FTIR data (KBr, pellet, cm-1): upsilon 3335, 3057, 2922, 1573,1436, 1243. 1H NMR (400 MHz, CDCl3,ppm): delta 3.94 (t,2H, CH2,J 47.8 Hz), 4.59 (t, 2H, CH2),6.85 (t, 2H, Py-H),6.87 (d, 2H, Py-H, J 7.1 Hz), 7.15 (d, 2H, Ph-H), 7.26 (t,1H, Ph-H), 7.54 (t, 2H, Ph-H), 7.57 (t, 2H, Py-H), 8.33 (d,2H, Py-H). 13C NMR (100 MHz, CDCl3,ppm): delta 42.83,67.63, 115.72, 116.79, 117.17, 121.13, 130.02, 137.32,147.14, 157.30, 159.39. ESI-MS (m/z): 291.16 [L1 + H]+.Anal. Calcd for C18H17N3O(Found) %: C, 74.23 (74.01); H,5.84 (5.71); N, 14.43 (14.13).

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; Wang, Jun; Liu, Jinyi; Chen, Liduo; Lan, Tianyu; Wang, Libo; Transition Metal Chemistry; vol. 44; 7; (2019); p. 681 – 688;,
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Reference of 64115-88-4, 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. 64115-88-4 name is 1-Bromo-2-(trifluoromethoxy)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.

Synthesis of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone To a flame-dried 100 ml round bottomed flask was added 1-bromo-2-(trifluoromethoxy)benzene (2.39 g, 9.9 mmol). The flask was fitted with a rubber septum, purged with nitrogen then charged with anhydrous THF (20 ml). The solution was cooled to -78 C. for 10 min, then a 2.5 M solution of n-butyl lithium in hexanes (3.9 ml, 9.8 mmol) was added dropwise over 3 minutes. The resulting solution was stirred at -78 C. for 40 minutes under nitrogen, then a solution of 739 mg (2.84 mmol) of 2-amino-5-bromo-N-methoxy-N-methyl-nicotinamide in 5 ml of THF was added dropwise over 3 minutes. The resulting red solution was allowed to warm to room temperature over 5 hours, then the reaction was quenched by addition of 10 ml of a saturated aqueous solution of ammonium chloride. Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes gave 530 mg (52%) of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone as a yellow-orange solid. 1H-NMR (CDCl3) delta=8.29 (d, 1H), 7.60 (m, 2H,), 7.45 (t, 1H), 7.42 (m, 3H), 1.79(br. s, 2H); MS m/z: 361 [MH]+.

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

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2006/30583; (2006); A1;,
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Application of 2398-37-0,Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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 round-bottomed flask was charged acetyl chloride (4.20g, 53.56mmol, leq), AICI3 (7.13g, 53.56mmol, leq), and carbon disulfide (80mL). To the mixture was added dropwise a solution of 3-bromoanisole (9.75g, 52.13mmol) in carbon disulfide (20mL) and stirred for 16 h. The resulting solution was diluted with ice water (l OOmL) and extracted with CH2G12 (50mLx3). The extracts were washed with H20, brine, and IN NaOH (30mL). The organic layer was dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes = 1 :10) to afford the title compound (6.2g, 51%).1H NMR (300MHz, CDC13) delta 7.48(dd, J = 8.4Hz, 1,2Hz, 1H), 7.04(brs. 1H), 6.76(dd, 1H), 3.74(s, 3H), 2.52(s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-methoxybenzene, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; HEO, Jung Nyoung; BAE, Myung-Ae; KIM, Nack Jeong; CHANG, Sung Youn; KANG, Namsook; YOO, Sung Eun; HWANG, Eun Sook; WO2011/30955; (2011); A1;,
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Synthetic Route of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 (1,3-dioxoisoindolin-2-yl)potassium (10.0 g, 53.9 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (37.5 g, 161 mmol) in acetone (250 mL) was stirred at 60 C. for 12 h. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography to give the title compound (12.0 g, 74% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.91-7.84 (m, 2H), 7.77-7.72 (m, 2H), 3.96-3.90 (m, 2H), 384-377 (m, 4H), 3.42 (t, J==6.0 Hz, 21-).

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

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 104-92-7, name is 1-Bromo-4-methoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-methoxybenzene

General procedure: A mixture of Ni(cod)2 (0.050 mmol), SIPr·HCl (0.050 mmol),KOt-Bu (0.050 mmol), and CPME was stirred at 100 C for 30min. To this was added NaOAc (0.85 mmol), aryl bromide 1(0.50 mmol), and N-TMS-carbazole 2 (0.65 mmol). The reactionmixture was quenched with H2O. The aqueous layer wasextracted with Et2O and washed with brine. The combinedorganic layers were dried over anhydrous MgSO4. After concentrationin vacuo, the residue was purified by flash chromatographyon silica gel or preparative TLC to afford N-aryl-carbazoles 3.

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; Minami, Yasunori; Komiyama, Takeshi; Shimizu, Kenta; Uno, Shu-Ichi; Hiyama, Tamejiro; Goto, Osamu; Ikehira, Hideyuki; Synlett; vol. 28; 18; (2017); p. 2407 – 2410;,
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Reference of 437-83-2,Some common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

Hydrobromic acid (48% in water, 140 mL) is added slowly to an aliquot of 11 (14. 33 g, 101. 5 mmol) cooled to 0 C. The resulting solid is broken up with a glass rod and stirred vigorously at 0 C for 10 min. A solution of sodium nitrite (7. 40g, 107. 2 mmol) in water (50 mL) is added slowly (-1. 5 h) to the stirred slurry containing 3-fluoro-2- methoxyphenylamine and hydrobromic acid, maintaining the temperature of the reaction mixture below 5 C. A purple solution of cuprous bromide (9. 62 g, 67. 1 mmol) in hydrobromic acid (48% in water, 50 mL) is added dropwise to the reaction mixture, maintaining the temperature of the reaction mixture below 5 C. The resulting reaction mixture is heated at 60 C until the evolution of gas ceases (-2. 5 h). The reaction mixture is cooled to room temperature, and the product extracted with diethyl ether (6 x 150 mL). The combined organic extracts are washed with brine (3 x 150 mL), dried over magnesium sulfate, and evaporated under reduced pressure to give 1-BROMO-3-FLUORO-2-METHOXYBENZENE as a brown oil. This product is of sufficient purity (295% by NMR spectroscopy) to use directly in the next synthetic STEP. 1H NMR (CDCl3) : No.3. 95 (d, JH-F= 1.5 Hz, 3H, OCH3), 6. 88 (apparent t OF D, JH-H = 8. 0 Hz, JH-F = 5. 5 Hz, 1H, H-5), 7. 04 (ddd, JH-F = 10. 5 Hz, JH-H = 8. 0 HZ, JH-H = 1. 5 Hz, 1H, H-4), 7. 30 (d of apparent T, JH-H = 8. 0 Hz, JH-H = 1. 5 Hz, JH-F = 1. 5 Hz, 1H, H-6). I9F {LH} NMR (CDCl3) : S-127. 7 (s). 13C {IH} NMR (CDCl3) : 1561. 4 (d, JC-F= 5. 0 Hz, OCH3), 116. 2 (d, JC-F = 19. 5 Hz, C-4), 117. 7 (D, JC-F = 3. 0 Hz, C-1), 124. 5 (d, JC-F = 8. 0 Hz, C-5), 128. 5 (D, JC-F = 3. 5 Hz, C-6), 145. 7 (d, Jc-F = 12. 5 Hz, C-2), 156. 2 (d, JC-F = 250. 5 Hz, C-3).

The synthetic route of 437-83-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2005/19228; (2005); A1;,
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