Ethers-buliding-blocks

Electric Literature of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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 suspension of the phenoxypropyl bromide (44) (0.3 mL, 1.90 mmol, d=1.365), piperidone hydrochloride hydrate (0.44 g, 2.86 mmol), K2CO3 (1.05 g, 7.62 mmol), anhydrous Na2SO4 (0.54 g, 3.81 mmol) and KI (47 mg, 0.286 mmol) in MeCN (20 mL) was stirred at reflux conditions for 2.5 hrs. The mixture was cooled to RT, diluted with water and extracted with EA. The extract was dried over Na2SO4, filtered, concentrated and the residue was purified by flash column chromatography, eluent 5percent MeOH in EA, to afford title compound 45 (0.45 g, quant. yield) as oil. (0383) 1H NMR: 500 MHz, CDCl3, delta (ppm): 7.30-7.26 (m, 2H), 6.96-6.90 (m 3H), 4.06 (t, J=6.3 Hz, 2H), 2.78 (t, J=6.1 Hz, 4H), 2.66 (t, J=7.1 Hz, 2H), 2.46 (t, J=6.8 Hz, 4H), 2.04-1.99 (m, 2H). MS: 233.3 (calcd.), 234.1 (M+H+, found).

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

Reference:
Patent; Mirati Therapeutics, Inc.; Marx, Matthew Arnold; Vaisburg, Arkadii; Christensen, James Gail; Galemmo, JR., Robert Anthony; (91 pag.)US2017/183308; (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. 19056-41-8, name is 3-Bromo-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-4-methoxyaniline

Example 31 STR39 2-Bromo-1-methoxy-4-pentafluorophenylsulfonamidobenzene. 1 H NMR (CDCl3): 7.35(d, J=3 Hz, 1H), 7.15(dd, J=9 Hz, 3 Hz, 1H), 6.97 (s, 1H), 6.81(d, J=9 Hz, 1H), 3,88 ppm (s, 3H). EI m/z: 433(35, M+), 202(100). The compound was prepared by a protocol similar to that of example 1 by replacing N,N-dimethyl-1,4-phenyldiamine dihydrochloride with 3-bromo-4-methoxyaniline.

The synthetic route of 19056-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tularik Inc.; US5880151; (1999); A;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 450-88-4

Step B: 4-fluoro-2-methoxybenzonitrile: To a solution of 1-bromo-4-fluoro-2-methoxybenzene(25 g, 0.12 mol) in 250 mL ofDMF was added Zn(CN)2 (28.6 g, 0.240 mol) and Pd(PPh3)4 (7.05g, 6.10 mmol) at one portion and the reaction was charged with Ar and heated to 100 C for 10 hours. Then the reaction was poured into IL ofEtOAc and filtered through a kieselguhr pad.The filtrate was washed with water, brine, dried and concentrated to solid, which was purified bysilica gel column to give 4-fluoro-2-methoxybenzonitrile.

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; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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 22094-18-4, Safety of 1,3-Dibromo-2,2-dimethoxypropane

To a stirred suspension of NaH (11.7 g, 293 mmol, 60% purity) in DMF (100 ml) was added diisopropylmalonic ester dropwise, keeping the temperature below 40 0C. The resulting mixture was stirred for 1 h at RT and then l,3-dibromo-2,2-dimethoxypropane (34.8 g, 133 mmol) was added in one portion. The resulting mixture was heated at 140 0C for 24 h and then cooled to RT. Saturated NH4Cl aqueous (400 ml) was added and the mixture extracted with hexane (2 x 190 ml). The combined organic phases were washed with H2O (2 x 250 ml) saturated NaHCO3 (2 x 250 ml), H2O (2 x 250 ml) and brine (250 ml). The organic phase was dried (Na2SO4), filtered and concentrated at reduced pressure to provide an orange oil. Purification by in vacuo distillation to remove excess of l,3-dibromo-2,2-dimethoxypropane (b.p. 60-62 0C, 0.1 mniHg) and diisopropylmalonic ester (b.p 78-80 0C, 0.1 mmHg) provided the title compound (20 g, 52%) as orange oil in the distillation flask. MS data: Calculated MH+ (289); Found 100% (MH+) m/z 289.NMR data: 1H NMR (360 MHz, CHLOROFORM- d) delta ppm 5.07 (2 H, spt, J=6.3 Hz), 3.16 (6 H, s), 2.70 (4 H, s), 1.24 (12 H, d, J=6.4 Hz).

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, 1,3-Dibromo-2,2-dimethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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 36942-56-0, Safety of 2-Bromo-4-methoxy-1-methylbenzene

2-bromo-4-methoxytoluene (100 mg, 0.5 mmol),Carbon tetrabromide (16mg, 0.05mmol) was addedInto a reaction flask filled with oxygen,Plug in an oxygen balloon,Finally add 10ml of acetonitrile,Reaction at 400nm LED wavelength and room temperature for 60h,After the reaction, the solvent was distilled off under reduced pressure.Add excess 2mol / L sodium hydroxide solution for washing,Adjust the pH to about 10 ~ 11,The aqueous phase was extracted multiple times with ethyl acetate,Then add 2mol / L of dilute hydrochloric acid to the water phase,Adjust the pH to 1-2,The aqueous phase was extracted again with ethyl acetate several times,Evaporate the ethyl acetate and dry,That gives compound 13,The yield was 78.5%.

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-Bromo-4-methoxy-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Li Xiaoqing; Zheng Kun; Xu Xiangsheng; (26 pag.)CN110563571; (2019); A;,
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Reference of 36449-75-9, These common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, 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.

General procedure: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
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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., Formula: C9H13NO2

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6g, 35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOBt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 mm stirring, to the reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixturewas stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with iN HC1 (100 mL), sat. NaHCO3 (100 mL) and brine (100 mL). The organic phase was then dried over MgSO4. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3g (78%). MS: [M+1] = 335.

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:
Patent; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; (400 pag.)WO2016/205739; (2016); A1;,
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Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); A1;,
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Application of 13101-88-7, 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 13101-88-7 as follows.

1.- 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3(2H)-one To a suspension of 2-amino-6-methoxynaphthalene (2.6 g, 15 mmol) in H2O (40 ml), HCl conc. was added (8 ml), it was cooled in an ice bath and a NaNO2 solution (1.19 g, 17.3 mmol) in H2O (18 ml) was added dropwise shaking the mixture at 0?C during 30 minutes. The previous solution was diluted in H2O (80 ml), 2,5-dimethylfuran-2,3-dihydrofuran-3-one (1.94 g, 17.3 mmol) was added and was left shaking during 2 hrs at room temperature resulting in a yellow precipitate. It was filtered, washed with water and dried. It was thereby obtained 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3-one (4.22 g, 95 %) in a solid crude form of an ocre-yellow color that was used directly in the following synthesis step. 1H-NMR (300 MHz, CDCl3) delta ppm: 8.35 (s, 1H), 7.85 (d, J=8,8Hz, 1H), 7.75-7.7 (m, 2H), 7.2 (m, 2H), 5.55 (s, 1H), 3.95 (s, 3H), 2.45 (s, 3H), 1.75 (s, 3H).

According to the analysis of related databases, 13101-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios Del. Dr. Esteve, S.A.; EP2113501; (2009); A1;,
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Synthetic Route of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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 1 : A solution of (S)-I -(4-methoxyphenyl)ethanamine (3.10 g, 20.5 mmol) in dichloromethane (30 ml) was cooled to -78 C and a solution of boron tribromide (3.88 ml, 41 mmol) in dichloromethane (15 ml) was added dropwise. The reaction mixture was stirred at -78 C for two hours and then at room temperature for 2 h. The solution was then cooled to 0 C and water (15 ml) was added followed by saturated aqueous sodium carbonate to pH 8. The mixture was partially concentrated by rotary evaporation, tetrahydrofuran (50 ml) was then added followed by di-tert- butyl dicarbonate (4.47 g, 20.5 mmol) and the reaction mixture was stirred at room temperature overnight. The water layer was extracted with ethyl acetate (2x 150 ml) and the combined organic layers were washed with brine, dried over sodium sulfate then filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes: ethyl acetate 4:1 to 3:1 as eluent to afford 1,1- dimethylethyl [(l S)-l-(4-hydroxyphenyl)ethyl]carbamate (2.90 g, 60 % yield). 1H NMR (400 MHz, CDCl3): 7.10 (br s, 2H), 6.73 (d, 2H), 6.07 (br s, IH), 4.91 -4.51 (m, 2H), 1.56-1.25 (m, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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