Tag: M.W=200-300

These common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-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. Recommanded Product: 261762-35-0

A 100-mL round-bottom flask charged with Pd2dba3 (69 mg, 0.075 mmol), BINAP (112 mg, 0.18 mmol), and NaOt_Bu (650 mg, 6.5 mmol) was degassed and filled with N2. THF (20 mL) was added, followed by a solution 5-bromo-l,2-difluoro-3-methoxybenzene (1.1 g, 5 mmol) and l-(2,5-dimethoxyphenyl)ethanone (1.08 g, 6 mmol) in THF (10 mL). The resulting mixture was heated at 70 C for 16 h. Water (30 mL) was added, and the mixture was extracted with ether (3 x 50 mL). The combined organics were dried over anhydrous Na2S04, filtered, and concentrated to give the crude product, which was purified by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate = 80/1 ~ 40/1) to give 2-(3,4-difluoro-5- methoxyphenyl)-l-(2,5-dimethoxyphenyl)ethanone (0.4 g) as a light yellow solid. ¾ NMR (CDCI3): delta 7.24 (d, 1H), 7.04 (dd, 1H), 6.92 (d, 1H), 6.68-6.61 (m, 2H), 4.23 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.78 (s, 3H); LCMS: 323 (M+H)+.

The synthetic route of 5-Bromo-1,2-difluoro-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Electric Literature of 52411-34-4,Some common heterocyclic compound, 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, molecular formula is C14H16N2O2, 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.

Compound 3 (2.44 g, 0.01 mol) was dissolved in MeCN(10 mL), then (i-Pr)2NEt (6 mL) and methyl bromoacetate (3 mL) were added to the mixture with stirring. The reaction mixture was refluxed for 24 h. After the reaction, the mixture was cooled down, poured into EtOAc (20mL), and filtered to remove the generated white solid. The combined EtOAc filtrates were concentrated in vacuo to give an oily solid, then adding a little methanol, white solid was generated, filtered, air dried and recrystallized in MeOH to give white solid 4.

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-Bis(o-aminophenoxy)ethane, its application will become more common.

Reference:
Article; Cheng, Zhao; Yang, Bingqin; Yang, Meipan; Zhang, Binglin; Journal of the Brazilian Chemical Society; vol. 25; 1; (2014); p. 112 – 118;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A mixture of 1 -bromo-4-fluoro-2-methoxybenzene (CAS No. [450-88-4]; 10.0 g, 48.8 mmol) in concentrated sulfuric acid (50 ml.) was cooled to 0 C and treated dropwise with a freshly prepared mixture of fuming nitric acid (1.05 eq., 2.1 ml_, 51 mmol) and concentrated sulfuric acid (1.85 eq., 4.8 ml_, 90 mmol). The reaction mixture was stirred at 0 C for 30 minutes and poured in small portions on ice water. The formed precipitate was filtered off, washed with cold water and kept. The filtrate was extracted with ethyl acetate and the organic layer combined with the isolated precipitation. The organic layer was dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (Si02-hexane/ ethyl acetate) to give the title compound (5.88 g, 44%). 1H-NM (400MHz, DMSO-de): delta [ppm] = 4.00 (s, 3H), 7.44 (d, 1 H), 8.40 (d, 1 H).UPLC- UPLC-MS (ESI-): [M – H]” = 248/250; Rt = 1.17 min (Br isotope pattern; Method E).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PANKNIN, Olaf; ZIMMERMANN, Katja; NEUHAUS, Roland; (162 pag.)WO2017/5674; (2017); A1;,
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Synthetic Route of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

The (S) -A40.2g (0.64mmol), 4- phenoxy-bromobenzene 0.24g (0.96mmol, 1.5eq.), Palladium acetate 0.013g (0.06mmol, 0.1eq.), BINAP0.037g (0.06mmol after, 0.1eq.), cesium carbonate 0.52g (1.6mmol, 2.5eq.) swap argon, DMF (4mL), the reaction 100 8 h, concentrated after adding saturated brine, extracted with methylene chloride and dried, Biotage silica gel column chromatography (petroleum ether / ethyl acetate = 28%) to give a pale yellow solid A70.27g, yield 87%.

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-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Nanjing Yong Shan Biological Technology Co., Ltd.; Wang Yazhou; Jin Qiu; Tang Feng; Huang Wei; Hua Yulin; (10 pag.)CN103113375; (2017); B;,
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Reference 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.

[0187] Into a 5 L 3-necked roundbottom flask, was placed a solution of l-(3- bromopropoxy)benzene (250 g, 1.16 mol) in THF (600 ml). To this was added dimethylamine in water (1 L 33percent). To the mixture was added KOH (200 g, 4.46 mol). The resulting solution was allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE = 1 :3). The resulting solution was extracted five times with 200 ml of EtOAc and the organic layers combined. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 20Og of crude N,N-dimethyl-3-phenoxypropan-l -amine as light yellow oil.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
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Synthetic Route of 19056-40-7, 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 19056-40-7 as follows.

Reference 2; Synthesis of 3-methoxy-4-(2-methylpyridin-4-yl)benzenamineStep l4-Bromo-3-methoxyaniline (3.70 g, 18.3 mmol; Aldrich) was dissolved in N,N- dimethylformamide (40 mL, 500 mmol) and triethylamine (2.68 mL, 19.2 mmol) was added. Acetic anhydride (1.81 mL, 19.2 mmol) was added and the reaction mixture stirred for 5 hours. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered and diluted with hexames. The layer was concentrated to minimal volume and the resultant slurry was filtered and washed with hexanes to yield N-(4- bromo-3-methoxyphenyl)acetamide as a light peach solids.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
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These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, 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. Recommanded Product: 588-63-6

General procedure: Bromoethane (0.45 mL, 6 mmol) was dropped to the mixture of 8 (0.86 g, 3 mmol), K2CO3 (0.83 g, 6 mmol) and KI (catalytic amount) in CH3CN. The mixture was stirred at 35°C for 8 h. he reaction mixture was filtered. The filtrate was concentrated and purified by chromatography on a silica gel column, eluting with a mixture of ethyl acetate and petroleum ether to give the desired product. 4.1.4.23. (E)-Ethyl 3-{5-[(biphenyl-4-ylmethyl)(3-phenoxypropyl)amino]methyl}furan-2-ylacrylate (12i). Compound 12i (1.29 g, 86.6percent yield) was synthesized from 11 (1.26 g, 3 mmol) and (3-bromopropoxy)benzene (0.77 g, 3.6 mmol) according to the procedure used to synthesize 9a; oil; MS (EI) m/z 495 (M+).

The synthetic route of (3-Bromopropoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Taotao; Wang, Hai; Su, Hong; Lu, Hui; Yu, Liqin; Zhang, Xiaojin; Sun, Haopeng; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5339 – 5354;,
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Adding a certain compound to certain chemical reactions, such as: 105529-58-6, name is 4-Bromo-2-fluoro-1-(trifluoromethoxy)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 105529-58-6, Recommanded Product: 4-Bromo-2-fluoro-1-(trifluoromethoxy)benzene

3-(3-fluoro-4-trifluoromethoxyphenyl)-2-methylpro panal [in the formula (II), W represents 3-fluoro-4-trifluoromethoxyphenyl group] was prepared using the method described by the reaction formula (D) . 7 mg (0.04 mmol) of palladium chloride (II) and 20 mg (0.076 mmol) of triphenylphosphine were dissolved in 2 ml of N,N-dimethylformamide at 120C under nitrogen atmosphere, and allowed to cool to 50C. The solution was admixed with 1.0 g (3.9 mmol) of 3-fluoro-4-trifluoromethoxybromobenzene, 420mg (5.8mmol) of methallyl alcohol and 390 mg (4.6 mmol) of sodium hydrogencarbonate, and was stirred at 130C for 3 hours. After standing to cool, the resultant solution was admixed with water and extracted with benzene. The separated benzene phase was washed with water and saturated brine successively, and dried over sodium sulfate anhydride. After solvent removal by distillation under a reduced pressure, 870 mg of an oily substance was obtained. The oily substance was purified by using silica gel column (Merck Silica gel 60, 230-400 mesh, Merck Co., eluent composition: Hexane/AcOEt=15/1). This gave 500 mg of 3-(3-fluoro-4-trifluoromethoxyphenyl)-2-methylpropanal as an oily substance. The yield was 51.3%.

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; KUREHA KAGAKU KOGYO KABUSHIKI KAISHA; EP1375483; (2004); A1;,
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Electric Literature of 13940-96-0, 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. 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of Intermediate AC (395 mg,1 .97 mmol) in EtOH (10 mL) was added 1,3- bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (427 mg,2.07 mmol),and the mixture was heated to reflux for 18h. After cooling to r.t.,Eta0 was added and the resultant solid collected by filtration (washing with EtOH/Et20) to afford the title compound as an off-white solid (436 mg,78%).1H NMR 6H (500 MHz,DMSO-d6) 11 .61 (br s,2H),7.40 (d,J = 8.5 Hz,1 H),7.38 – 7.32 (m,2H),7.09 – 7.03 (m,2H),6.97 – 6.92 (m,2H),6.81 (dd,J = 8.5,2.4 Hz,1 H),3.75 (s,3H); LCMS (Method A): 3.24 min,(284.2,MH+).

The synthetic route of 4-Phenoxybenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBACHEM NV; URCH, Christopher, John; JACKSON, Victoria, Elizabeth; JORDAN, Linda; BURGIN, Ryan, Neil; (180 pag.)WO2019/141980; (2019); 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 19056-40-7

Intermediate 235; Diethyl IFf 4-bromo-3-methoxyphenyl)amino1methylenelmalonate; To a solution of 4-bromo-3-methoxyaniline (25 g, 0.12 mol) in CH3CN (150 mL) was added diethylethoxymethylene malonate (27 mL, 0.13 mol). After 20 hours, the solvent was removed under reduced pressure and the residue dissolved in EtOAc. Hexane was added, and the resulting precipitate collected to give 37 g (80percent) off-white solid. 1H NMR: 10.68 (d, 1 H), 8.38 (d, 1 H), 7.52 (d, 1 H), 7.20 (d, 1 H), 6.91 (dd, 1 H), 4.20 (q, 2 H), 4.11 (q, 2 H), 3.86 (s, 3 H), 1.23 (m, 6 H); m/z: 372.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/119046; (2007); A1;,
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