Ethers-buliding-blocks

Application of 6443-69-2,Some common heterocyclic compound, 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, molecular formula is C10H14O3, 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: BF3¡¤Et2O was slowly added dropwise, to a stirred solution of polyhydroxy or polymethoxy phenols and alkyl alchol in dioxane at 0C. After the addition was completed, the stirring was continued for 3h at room temperature. The mixture was poured water and extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure. The crude was chromatographed on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,3-Trimethoxy-5-methylbenzene, its application will become more common.

Reference:
Article; Kamauchi, Hitoshi; Oda, Takumi; Horiuchi, Kanayo; Takao, Koichi; Sugita, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, 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 393-15-7, category: ethers-buliding-blocks

4-Methoxy-3-trifluoromethyl-phenylamine (5 g, 26 mmol) in 12 mL water was cooled to -5 degrees C (Ice/Methanol bath). Conc. HCl was added dropwise (7 ml), and the reaction mixture was stirred for five minutes. A solution of NaNO2 (2.0 g, 29 mmol) dissolved in 3 ml water was added dropwise over 10 minutes, and the reaction mixture was tirred for 30 min. Sodium acetate (1.8 g, 22 mmol) was then added, and stirring was continued at -5 degrees C. In a separate flask, ethyl alpha-acetoacetate (4.55 g, 29 mmol) in 20 ml absolute ethanol was stirred, and KOH (1.6 g, 29 mmol) dissolved in 3 ml water was added, followed by ice (30 g). The resulting diazonium salt was added quickly to the reaction mixture, rinsing in with 5 ml EtOH, and the reaction mixture was stirred at zero degrees C for 3.5 hours, then stored at -10 C) for 16 hours. The reaction mixture was warmed to room temperature and extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure to leave a liquid residue. In a separate flask 100 ml EtOH and 21 ml acetyl chloride were mixed, with cooling in an ice bath, then heated to 70 degrees C. The liquid residue was added via pipette over 15 minutes to the acetyl chloride solution. This reaction mixture was heated to reflux for 2.5 hours, cooled, evaporated under reduced pressure. The residue was purified by colunm chromatography (10% ethyl acetate/hexane) to give 3.0 g 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester, 38% as a white solid. and triturated with diethyl ether to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (1.0 g) as a white solid, and 5-Methoxy-3-methyl-4-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (14% ) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-3-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2005/209260; (2005); 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. 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 41864-45-3

EXAMPLE 157 4-(4,5-Dimethoxy-2-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4,5-dimethoxy-2-methylaniline (48 mg, 0.290 mmol) similar to Example 117 and isolated as a red solid (8 mg, 11%). 1H NMR (CDCl3): 9.69 (s, 1H), 8.74-8.68 (m, 2H), 7.56 (s, 1H), 7.43-7.39 (m, 1H), 6.84 (s, 1H), 6.83 (s, 1H), 6.46 (s, 1H), 3.94 (s, 3H), 3.86 (s, 3H), 2.23 (s, 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; Cytovia, Inc.; US2003/69239; (2003); A1;,
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Electric Literature of 2062-98-8, A common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, molecular formula is C6F12O2, 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.

EXAMPLE 2: Example for preparation of CF3CF2CF2OCF (CF3) CF2OCOCF (CF3) OCF2CF2CF3 (1b) (fluorination step)[0090] Compound (3b) (200.0 g) obtained in Example 1, was dissolved in CF3CF2CF2OCF(CF3)COF (hereinafter referred to as compound (4b), 1000.0 g). On the other hand, into a 3000 mL autoclave made of nickel, NaF powder (260.5 g) was. put, and compound (4b) (2000.0 g) was added, followed by stirring and cooling to -10 DEG C. After supplying nitrogen gas for 1 hour, fluorine gas diluted to 20% with nitrogen gas, was supplied at a flow rate of 22.59 L/hr for 1 hour, and while supplying it at the same flow rate, the above fractional solution was injected over a period of 60 hours. [0091] Then, while supplying fluorine gas diluted to 20% with nitrogen gas, while maintaining the above flow rate, 20 mL of a solution of compound (4b) in benzene (0.01 g/mL) was injected, the outlet valve of the autoclave was closed, and when the pressure became 0.12 MPa, the inlet valve of the autoclave was closed, followed by stirring for 1 hour. Further, such an operation was repeated 4 times during a period until the temperature rose from -10 DEG C to room temperature and thereafter 5 times at room temperature. During the period, benzene was supplied in a total of 1.800 g, and compound (4b) was injected in a total of 281.0 g. Thereafter, nitrogen gas was supplied for 2 hours, and the reaction mixture was taken out by decantation. The obtained crude liquid was concentrated by an evaporator, and the product was quantified by <19>F-NMR, whereby it contained CF3CF2CF2OCF (CF3) CF2OCOCF (CF3) OCF2CF2CF3 (compound (1b)) in a yield of 69%. A part of the crude liquid was taken and distilled under reduced pressure to obtain compound (1b) . The boiling point of compound (1b) was from 46 to 51 DEG C/5.2 kPa.; EXAMPLE 3: Example for preparation of compound (1b) by a continuous process[0092] Using compound (2b) (75.5 g, 0.640 mol) and compound (1b) obtained in Example 2 (213.1 g, 0.321 mol), the reaction was carried out in the same manner as in Example 1 to obtain compound (3b) (amount: 272.4 g, 0.634 mol). The yield of compound (3b) as quantified by <1>H-NMR, was 99%. Then, the compound (3b) was reacted with fluorine in the same manner as in Example 2 to obtain compound (1b) (amount: 294.0 g, 0.44 mol). The same operation was repeated to finally obtain 3000 g of compound (1b).

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASAHI GLASS COMPANY LTD.; EP1352892; (2003); A1;,
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Application of 41789-95-1, A common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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.

Step D: To a cold (0 C. ) and stirred solution of 3-methoxy-N-benzylamine (46 g, 305 mmol) and diisoproplyethylamine (40 mL, 276 mmol) in CH2Cl2 (500 mL) was added the product obtained from Step C (71 g, 276 mmol) in CH2Cl2 (500 mL) solution. The reaction was then stirred at 0 C. for 2 hours. It was washed with water (500 mL), saturated aqueous NaHCO3 (500 mL), brine, dried and concentrated to give the desired product as a light yellow liquid (107 g, crude, quant.): 1H NMR (300 Hz, CDCl3) delta 8.43 (s, 1H), 7.94-7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.40 (d, J=5.4 Hz, 1H), 7.25-7.21 (m, 1H), 6.93-6.80 (m, 3H), 3.83 (s, 2H), 3.76 (s, 3H), 3.67 (s, 2H), 2.40 (s, 3H); ESI-MS m/z 326 [M+H]+.

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.; US2006/52378; (2006); A1;,
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Electric Literature of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,2-Diethoxyethanamine

N- (2,2-Diethoxyethyl)carbodiimide; [0077] A solution of the aminoacetaldehyde diethyl acetal (13.16g, 99 mmol) in ether (35 mL) was added to a suspension ofCNBr (10.47g, 99 mmol) in hexane (35 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was removed by filtration and washed with ether. The combined filtrate was concentrated. Purification by column chromatography (silica gel, eluting with dichloromethane to 4% methanol in dichloromethane, gradient) afforded the title compound (7.0 g, 44.7%, one half of the starting amine served as a sacrificial base in the reaction) (Rf; 2.70, 4% methanol in dichloromethane, stain with 10% ethanolic molybdatophosphoric acid). 1H NMR 400 MHz (CDC13) 8 4.58 (t, J= 5.2 Hz, 1H), 3.77 – 3.69 (m, 2H), 3.65 (br, s, 1H), 3.60 – 3.52 (m, 2H), 3.16 (t, J= 5.6 Hz, 1H), 1.23 (t, 6H, J= 6.8 Hz).

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 645-36-3.

Reference:
Patent; IRM LLC; WO2005/123719; (2005); A1;,
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Reference of 126-38-5, A common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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.

[0186] A mixture of 3-bromobenzenethiol (630 muL, 5.33 mmol), l-bromo-2,2- dimethoxypropane (715 muL, 5.29 mmol), and K2CO3 (1.10 g, 7.96 mmol) in DMF (11 mL) was heated at 150 0C for 2.5 hours. The crude reaction mixture was cooled, filtered, and concentrated. The residue was purified using flash chromatography (0-30% ethyl acetate in hexanes) to afford the title compound as a clear oil (1.66 g, 108% with some trapped solvent). The material was used as is for the next reaction. [0187] 1H NMR (500 MHz, DMSO-J6) delta 1.33 (s, 3H), 3.12 (s, 6H), 3.25 (s, 2H), 7.25 (dd, J = 8.4, 7.5 Hz, IH), 7.36 (dd, J = 7.9, 1.9 Hz, 2H), 7.54 (t, J= 1.8 Hz, IH)

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; TARGEGEN INC.; WO2009/26345; (2009); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: ((3-Bromopropoxy)methyl)benzene

To a solution of methyl [2- (4-HYDROXYPHENOXY)-2-METHYLBUTANOATE] (5g, 22. [32MMOL)] in 30mL [DMF] was added cesium carbonate (8.7g, 26. [7MMOL)] followed by benzyl 3-bromopropyl ether (7.7g, 33.6mmol). The solution was stirred at 45 [XB0;C] for 24hr, cooled and poured over water. Extraction with AcOEt followed by washing the extracts with water, drying over anhydrous [NA2SO4] and concentrating under reduced pressure gave the crude residue. Purification over silica gel using AcOEt/hexanes furnished the desired alkylated derivative (8.25g). This product was taken up in [MEOH] (75mL) and hydrogenated over 10percent [PD/C] at 40psi to provide methyl [2- (4- (3-HYDROXYPROPOXY)] phenoxy) -2-methylbutanoate (6.23g, quantitative). [‘H-NMR] [(400MHZ,] [CDC13)] : [8] 6.82 (d, 2H, J=9.4Hz), 6.78 (d, 2H, J=9.2Hz), 4.08 (t, 2H, J=6. [1HZ),] 3.87 (t, 2H, J=6Hz), 3.79 (s, 3H), 2.06-1. 92 (m, 4H), 1.44 (s, 3H), 0.99 (t, 3H, J=7.4Hz).

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/10992; (2004); 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6BrFO

a) 3-Bromo-6-fluoro-2-methoxybenzoic acid I45 To a solution of diisopropylamine (5.4 g, 53.7 mmol) in THF (150 ml.) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 23.4 ml_, 58.5 mmol) dropwise and the mixture was stirred at -78 C for 1 h. The resulting mixture was added dropwise to a solution of 1-bromo-4-fluoro-2-methoxybenzene (10.0 g, 48.8 mmol) in THF (50 ml.) at -78 C and stirring was continued for 90 min. C02 was bubbled through the mixture for 20 min with stirring at -78 C, then allowed to warm to RT and stirred for 15 min. The reaction mixture was adjusted to pH=1 with HCI and the mixture was diluted with water and extracted with DCM (500 ml_). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH = 100/1 to 30/1) to give the title compound (8.0 g, 66%) as a colorless oil. LCMS-D: Rt2.12 min; m/z 248.9/250.9 [M+H]+.

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
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