Ethers-buliding-blocks

Reference of 70627-52-0,Some common heterocyclic compound, 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, molecular formula is C20H16FNO, 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 2): To a solution of TiCl4 (18.2 ml, 0.165 mol) in CH2Cl2 (600 ml) at 0 C., was added titanium isopropoxide (16.5 ml, 0.055 mol). After 15 min, the product of Step 1 (49.0 g, 0.17 mol) was added as a solution in CH2Cl2 (100 ml). After 5 min., diisopropylethylamine (DIPEA) (65.2 ml, 0.37 mol) was added and the reaction mixture was stirred at 0 C. for 1 h, the reaction mixture was cooled to -20 C., and 4-benzyloxybenzylidine(4-fluoro)aniline (114.3 g, 0.37 mol) was added as a solid. The reaction mixture was stirred vigorously for 4 h at -20 C., then acetic acid was added as a solution in CH2Cl2 dropwise over 15 min, the reaction mixture was allowed to warm to 0 C., and H2SO4 (2N) was added. The reaction mixture was stirred an additional 1 h, the layers were separated, washed with water, separated and the organic layer was dried. The crude product was crystallized from ethanol/water to obtain the pure intermediate.

The synthetic route of 70627-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2005/96307; (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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3-Dibromo-5-methoxybenzene

step 2-To a solution of 57b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (97:3 to 95:5) to afford 58.

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; Roche Palo Alto LLC; US2006/25462; (2006); 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. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., Recommanded Product: 2′-Methoxyphenyl acetylene

1-Ethynyl-2-methoxybenzene (2a, 265 mg, 2 mmol) and benzyl azide (266 mg, 2 mmol) were added to a 1 : 1 water-tert-butyl alcohol mixture (8 mL). A freshly prepared 1 M aqueous solution of sodium ascorbate (200 muL, 0.2 mmol) and an aqueous solution of CuSO 4 ¡¤ 5 H 2 O (65 muL, 5 mg, 0.02 mmol) were then added in succession, and the mixture was stirred for ~14 h at room temperature (TLC). The mixture was diluted with 30 mL of ice water and kept for 15 min in an ice bath, and the white precipitate was filtered off, thoroughly rinsed with cold water (2 ¡Á 15 mL), and dried under reduced pressure. Yield 474 mg (89%), off-white solid. 1 H NMR spectrum, delta, ppm: 8.11 s (1H), 7.58 d (2H, J = 7.4 Hz), 7.42 t (1H, J = 8.5 Hz), 7.34-7.28 m (3H), 7.16 d (1H, J = 7.1 Hz), 7.00-6.94 m (2H), 6.13 s (2H), 3.70 s (3H). 13 C NMR spectrum, delta C , ppm: 159.5, 139.5, 136.7, 131.6, 129.2, 128.5, 128.1, 126.5, 120.3, 109.2, 104.1, 56.1, 54.0. Mass spectrum: m/z 266.1214 [M + H] + . Calculated for C 16 H 16 N 3 O: 266.1217.

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jabeen; Khera; Iqbal; Asgher; Russian Journal of Organic Chemistry; vol. 55; 9; (2019); p. 1416 – 1422; Zh. Org. Khim.;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 sodium nitrite (1 .78 g, 25.87 mmol) in water (5 mL) was slowly added to a cooled (-10 C) suspension of 5-bromo-2-methoxyaniline (5.0 g, 24.87 mmol) in 6N HCI aq. (13 mL) so as to keep the internal temperature below 0 C. The mixture was stirred for another 20 mm at 0 C, then a solution of stannous chloride dihydrate (14.1 g, 72.1 mmol) in conc. aq. HCI (25 mL) was added slowly. The reaction mixture was stirred an additional 1 .5 h at 0 C. The pH of the reaction mixture was carefully adjusted to -8 with sat. aq. NaHCO3. The mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by trituration with pentane to give the title compound. MS (ESl+) m/z 217.0 (M(79Br)+H).

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher; EHARA, Takeru; (134 pag.)WO2017/103888; (2017); 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20781-20-8

General procedure: Amine (1 mmol), 2-aminothiophenol (2 mmol), BODIPY photosensitizer (0.01 mmol, 1.0 mol%), and acetonitrile (5 mL) were added to a dry 10-mL flask. The flask was pressurized with air (2 bar) and then heated to 50 C. The solution was then irradiated using a 35-W xenon lamp through a cutoff filter (0.72M NaNO2 aqueous solution, which is transparent for light >385nm, because lamps could emit a small amount of ultraviolet light). After the reaction was completed, the solvent was evaporated under reduced pressure. The crude product was further purified using column chromatography.

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 20781-20-8.

Reference:
Article; Zhou, Zeyin; Yang, Weijun; Synthetic Communications; vol. 44; 21; (2014); p. 3189 – 3198;,
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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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Methoxy-5-(trifluoromethyl)aniline

EXAMPLE 22 3-{4-[3-(2-Methoxy-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide 82.4 mg (0.278 mmol) of triphosgene, followed by 0.223 cm3 of triethylamine, are added, at a temperature in the region of 20 C., under an argon atmosphere, to 0.2 g (0.793 mmol) of 3-(4-aminophenyl)-1H-pyrrolo-[3,2-b]pyridine-2-carboxamide in solution in 18 cm3 of tetrahydrofuran. After stirring for 1 hour at a temperature in the region of 20 C., 182 mg (0.952 mmol) of 2-methoxy-5-trifluoromethylphenylamine in solution in 17 cm3 of tetrahydrofuran are added. After stirring for 16 hours at a temperature in the region of 20 C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give a residue which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile] (90/5/5 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 109 mg of 3-{4-[3-(2-methoxy-5-trifluoromethylphenyl)ureido]-phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide are obtained in the form of a yellow solid that melts at around 194 C.; 1H NMR (300 MHz, (CD3)2SO d6, -delta in ppm): 3.99 (s: 3H); 6.97 (broad s: 1H); from 7.18 to 7.27 (m: 2H); 7.33 (dd, J=9 and 1 Hz: 1H); 7.56 (d, J=9 Hz: 2H); 7.63 (d, J=9 Hz: 2H); 7.66 (very broad s: 1H); 7.81 (dd, J=8 and 1.5 Hz: 1H); 8.40 (dd, J=4.5 and 1.5 Hz: 1H); 8.58 (m: 2H); 9.56 (s: 1H); 11.88 (very broad s: 1H). MS-ES+: m/z=470(+)=(M+H) (+).

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; AVENTIS PHARMA S.A.; US2007/259910; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 25245-34-5,Some common heterocyclic compound, 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

2-Bromo-1,4-dimethoxybenzene 39a (250 mg, 1.15 mmol), 2-formylphenylboronic acid 34 (207 mg, 1.38 mmol), tetrakis(triphenylphosphine)palladium(0) (133 mg, 0.29 mmol) and CsF (437 mg, 2.88 mmol) were added to a microwave vial in dimethoxyethane (2 mL) as solvent and the solution was degassed for 2 min. The reaction mixture was transferred to a microwave reactor at 150 C and 150 W power with vigorous stirring for 30 min. On completion, the reaction mass was filtered off, adsorbed on silica and subjected to column chromatography (5% EtOAc/Hexane) to yield the product 40a as white low melting solid (246 mg, 1.02 mmol, 88%). 1H NMR (500 MHz, CDCl3) d 9.79 (1H, s, CHO), 8.01-7.97 (1H, m, ArH), 7.64 (1H, td, J = 7.5, 1.2 Hz, ArH), 7.48 (1H, t, J = 7.6 Hz, ArH), 7.38-7.34 (1H, m, ArH), 6.94 (1H, dd, J = 8.9, 3.0 Hz, ArH), 6.90 (1H, d, J = 8.9 Hz, ArH), 6.87 (1H, d, J = 3.0 Hz, ArH), 3.81 (3H, s, OMe), 3.67 (3H, s, OMe); 13C NMR (126 MHz, CDCl3) d 192.5, 153.8, 150.7, 141.6, 134.0, 133.7, 131.0, 127.8, 127.7, 126.6, 117.3, 114.4, 111.8, 55.9, 55.8.

The synthetic route of 25245-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pradeep, Priyamvada; Ngwira, Kennedy J.; Reynolds, Chevonne; Rousseau, Amanda L.; Lemmerer, Andreas; Fernandes, Manuel A.; Johnson, Myron M.; de Koning, Charles B.; Tetrahedron; vol. 72; 51; (2016); p. 8417 – 8427;,
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. 634-36-6, name is 1,2,3-Trimethoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H12O3

General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.

The synthetic route of 634-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-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 29578-39-0, HPLC of Formula: C7H6BrFO

To a solution of Compound 187 (0.700 g, 3.41 mmol) in 1,4-dioxane (5 ml) were added Compound 188 (0.861 g, 4.10 mmol) and PdCl2(dtbpf) (0.223 g, 0.341 mmol), and then 2 mol/L aqueous solution of potassium carbonate (2.561 ml, 5.12 mmol), and the reaction mixture was stirred at 70C. After completion of the reaction, water was added to the reaction mixture, and the resulting mixture was extracted with chloroform, which was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Compound 189 (0.667 g, 93.8%). Compound 189; Method B LC/MS retention time = 1.99 min. MS (ESI) m/z = 209.35(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-fluoro-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; TAMURA, Yuusuke; HINATA, Yu; KOJIMA, Eiichi; OZASA, Hiroki; (241 pag.)EP3187498; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, Safety of (Triethoxymethyl)benzene

General procedure: The starting hydrazide 4, 8e-i (10 mmol) was added to a mixture of the appropriate triethyl orthoester (10 mol) and 0.1 g p-TsOH in 20 mL of xylene and kept under reflux for 3 h (TLC). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane/AcOEt, 1:2 v/v) or crystallised from benzene/hexane mixture.

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:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Ejsmont, Krzysztof; Tetrahedron; vol. 67; 40; (2011); p. 7838 – 7845;,
Ether – Wikipedia,
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