Category: ethers-buliding-blocks

Synthetic Route of 35822-58-3, 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. 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, This compound has unique chemical properties. The synthetic route is as follows.

To a cooled solution of 5 g (1 9.3 mmol) of 1 -bromo-2-(diethoxymethyl)benzene in 40 mL of diethylether, are slowly added 12 mL (1 9.3 mmol) of a 1 .6 M solution of butyllithium. The reaction mixture is stirred at ambient temperature for 1 hr. After slow addition of 4.28 g (25 mmol) of chloro(dimethyl)phenylsilane, the reaction mixture is further stirred for 2 hrs at ambient temperature, then poured over a mixture of ice and 40 mL of 1 N HCI and stirred overnight. The watery layer is extracted with 2 x 50 mL of ethyl acetate. The organic layer is washed twice by a concentrated aqueous solution of NaCI and dried over magnesium sulfate to yield after concentration, 5.45 g of a yellow oil. Column chromatography on silica gel (gradient n-heptane/ethyl acetate) yields 4.65 g (100% yield) of 2-[dimethyl(phenyl)silyl]benzaldehyde as a colorless oil. (M+H = 241 ).

The chemical industry reduces the impact on the environment during synthesis 2-Bromobenzaldehyde diethyl acetal. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AG; CRISTAU, Pierre; DESBORDES, Philippe; ES-SAYED, Mazen; GROSJEAN-COURNOYER, Marie-Claire; LACHAISE, Helene; RINOLFI, Philippe; SCHMIDT, Jan-Peter; TSUCHYIA, Tomoki; VORS, Jean-Pierre; WO2013/156560; (2013); A1;,
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Related Products of 1516-96-7, 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. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection, to a 250 mL dry 3-necked round bottom flask equipped with a magnetic stirrer and thermometer was added:THE was added dropwise to the solution of the residue prepared above under nitrogen at 0C. After stirring another 1.5h at room temperature, the mixture was quenched withwater at 0C and extracted three times withdichloromethane. The combined organic layers were dried over Na2504 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate = 75:25, to give product as a white solid (1.94 g, 81% yield).1.0 g tetraethyl (((2R)-propane-1,2-diylbis(oxy))bis(3,1-phenylene))bis(phosphonate) (2.0 mmol, 1.0 equiv.) in3.0 mL thionyl chloride (40.0 mmol, 20.0 equiv.) under nitrogen was added30.0 iL dimethylformamide (0.4 mmol, 0.2 equiv). The mixture was stirred under reflux for 18 h, during which time15.0 iL dimethylformamide (all together 8.0 mmol, 0.3 equiv.) was added after 12h. After the solvent was evaporated, the residue was dissolve in5.0 mL THE and concentrated in vacuo (once). The residue was used for the next step without further purification.To a phenyl magnesium bromide solution prepared from a suspension of0.53g magnesium turning (22.0 mmol, 11.0 equiv.) and6.0 g 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (20.0 mmol, 10.0 equiv.) in20.0 mL10.0 mL50 mL

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DSM IP ASSETS B.V.; BONRATH, Werner; FENG, Zheng-Chuan; MEDLOCK, Jonathan, Alan; PENG, Kun; ZHU, Zhibin; (28 pag.)WO2018/189107; (2018); A1;,
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Synthetic Route of 104-92-7, The chemical industry reduces the impact on the environment during synthesis 104-92-7, name is 1-Bromo-4-methoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred solution of 1.0 mmol of aryl halide in 4 mL of DMF,1.0 mmol of terminal alkyne, 1.5 mmol of piperidine and 0.2 mol%of Pd/Fe3O4NPs were added and the mixture was heated on anoil bath at 110C for 24 h under inert atmosphere (N2). After com-pletion of the reaction (as monitored by TLC), the reaction mixturewas cooled to room temperature and the catalyst was separatedusing a magnetic separator. The solvent was evaporated at reducedpressure, and the residue was subjected to gel permeation chro-matography to afford pure products. All the products are knowncompounds and the spectral data and melting points were identicalto those reported in the literature

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

Reference:
Article; Nasrollahzadeh, Mahmoud; Mohammad Sajadi; Rostami-Vartooni, Akbar; Khalaj, Mehdi; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 31 – 39;,
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Reference of 62415-74-1,Some common heterocyclic compound, 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, molecular formula is C7H6Br2O, 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.

Synthesis of Intermediate I-1 (0258) 5.31 g (20.0 mmol) of 1,2-dibromo-4-methoxybenzene, 3.30 g (30.0 mmol) of pyrocatechol, 0.190 g (1.0 mmol) of CuI, 0.264 g (1.0 mmol) of 18-crown-6, and 8.28 g (60.0 mmol) of K2CO3 were dissolved in 150 mL of dimethylformamide (DMF), and stirred at a temperature of about 140 C. for about 24 hours. The solution was cooled to room temperature, 60 mL of water was added thereto, and an organic layer was extracted three times therefrom using 60 mL of diethyl ether. The obtained organic layer was dried using magnesium sulfate (MgSO4), and the MgSO4 was removed by filtration. A solvent was next removed therefrom by evaporation. The obtained residue was separated and purified through silica gel chromatography to produce 3.21 g of Intermediate I-1 (yield: 75%). The obtained compound was identified by liquid chromatography-mass spectrometry (LC-MS). C13H10O3: M+1 215.1

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-methoxybenzene, its application will become more common.

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Youngkook; Jung, Hyejin; Han, Sanghyun; Hwang, Seokhwan; (115 pag.)US2017/77419; (2017); A1;,
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Application of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15-9: Preparation of 2-(4-methyl-2-nitro-phenyl)-thiazole (65).; The procedure described in Example 15-1 was followed except that 4-methyl-2-nitro- thiobenzamide (56) was used instead of 4-trifluoromethyl-2-nitro-thiobenzamide, bromoacetaldehyde-dimethylacetal was used instead of 1 -bromo-3-methyl-butan-2-one, and the reaction was acid catalyst with 5% acetic acid. This gave the title compound (66 mg, 75%). LC/MS: (Method I): tR= 0.98 min, >90%, m/z (ESI+)= 221 (MH+).

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

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14922; (2007); A1;,
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Synthetic Route of 39538-68-6, The chemical industry reduces the impact on the environment during synthesis 39538-68-6, name is 2-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

Iron (5.35 g, 95.7 mmol) was added to a solution of 2-nitro-5-methylanisole (10, 4.00 g, 23.9 mmol) in ethanol (60 ml) and 6 M aqueous hydrochloric acid (30 ml), and the mixture was heated at reflux for 2 h. The reaction mixture was diluted with ethyl acetate and filtrated through Celite. Evaporation of the filtrate afforded crude 11. NaNO2 (2.11 g, 30.6 mmol) was added to a solution of crude 11 (2.80 g, 20.4 mmol) in THF (80 ml) and 4 M aqueous hydrochloric acid (40 ml) at 0 C. After 30 min, potassium iodide (4.80 g, 30.6 mmol) was added, and the mixture was heated at reflux for 3 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate and brine, dried with sodium sulfate, and evaporated. Purification by silica gel column chromatography (n-hexane/ether 100:1 to 98:2) gave 12 (pale yellow oil, 3.77 g, 15.2 mmol, 65% for two steps). 1H NMR (500 MHz, CDCl3) delta 7.60 (d, 1H, J=7.9 Hz), 6.63 (d, 1H, J=1.2 Hz), 6.53 (dd, 1H, J=7.9, 1.2 Hz), 3.84 (s, 3H), 2.31 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 157.84, 139.86, 138.96, 123.36, 112.07, 81.78, 56.18, 21.42; HRMS (FAB+) m/z 248.9780 [(M+H)+: calcd for C8H10OI, 248.9776].

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Iwashita, Masazumi; Fujii, Shinya; Ito, Shigeru; Hirano, Tomoya; Kagechika, Hiroyuki; Tetrahedron; vol. 67; 33; (2011); p. 6073 – 6082;,
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Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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. category: ethers-buliding-blocks

A 250 mL round-bottomed flask was charged with 5-bromo-2-methoxy-phenol ( 1 .5 g, 76.4 mmol), l -bromo-3-methoxy-propane (12.9 g, 84 mmol), K >C( , (22 g, 2 153 mmol) and DM F (50 mL). The resultant mixture was stirred at 50 C for 3 hours, and then ethyl acetate and water was added. The organic phase was separated, and then dried over anhydrous Na?SO.and then concentrated to give 4-bromo- l -methoxy-2-(3-methoxypropoxy)benzene (23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; YANG, Song; HAN, Xingchun; WANG, Zhanguo; (96 pag.)WO2015/173164; (2015); A1;,
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Reference of 36865-41-5, 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 36865-41-5 as follows.

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine.To a suspension of Mg (911 mg, 37.5 mmol) and iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of l-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard- formation started. The rest of the l-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard-sol. (IM in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4- dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 0C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane – > EtO Ac/heptane 1 :1) yielded the title compound (1.51 g, 62%). LC-MS: tR = 0.80 min; ES+: 260.15.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); 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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H8F3NO

d) Preparation of Intermediate 4 3-Methoxy-5-(trifluoromethyl)benzenamine (20 g, 104.6 mmol) was added portion-wise to a cooled solution of NaNO2 (7.392 g, 107.1 mmol) in H2SO4 (74 ml) and CH3COOH (88 ml). This mixture was added dropwise to a vigorously stirred solution of CuBr (18 g, 62.8 mmol) in 48% HBr (200 ml) at 0 C. The r.m. was stirred for 45 min at r.t. and was then poured into ice-water. This aqueous mixture was extracted with DCM. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated at low temperature. The residue was stirred in a NaHCO3 solution and extracted with DIPE. The separated organic layers was dried (MgSO4), filtered and the solvent was evaporated. Yield: 12.7 g of intermediate 4 (yield 48%).

The synthetic route of 349-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacDonald, Gregor James; Thuring, Johannes Wilhelmus John F.; Van den Keybus, Frans Alfons Maria; Van Roosbroeck, Yves Emiel Maria; US2012/172354; (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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7FO

Step 1: Preparation of 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one. A suspension of aluminum chloride (9.4 g, 70.5 mmol) in a solution of 2-fluoroanisole (6.6 mL, 58.8 mmol) and anhydrous chloroform (200 mL) was cooled to 0 C. under a blanket of dry nitrogen. A solution of phenylacetyl chloride (8.6 mL, 64.7 mmol) in anhydrous chloroform (50 mL) was added to the vigorously stirred suspension over 20 minutes keeping the reaction temperature <5 C. The yellowish solution was stirred at 0 C. for 1 hour, poured into ice (200 mL) and stirred without temperature control for 16 hours. The layers were separated, and the aqueous layer was extracted with dichloromethane (2*100 mL). The combined organic solution was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting solid was recrystallized from boiling hexane to yield, upon filtration and drying, 1-(3-fluoro-4 methoxyphenyl)-2-phenyl-ethan-1-one (12.9 g, 90%) as white crystals: 1 H NMR (CDCl3 /300 MHz) delta 7.82-7.72 (m, 2H), 7.35-7.24 (m, 5H), 6.98 (dd, J=8.46, 8.26 Hz, 1H), 4.22 (s, 2H), 3.94 (s, 3H). 19 F NMR (CDCl3 /282.2 MHz) -134.875 (m). According to the analysis of related databases, 321-28-8, the application of this compound in the production field has become more and more popular. Reference:
Patent; G. D. Searle & Co.; US5859257; (1999); A;,
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