Tag: M.W=200-300

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., SDS of cas: 450-88-4

To a mixture of magnesium (0.79 g, 32.5 mmol) and lithium chloride (1.52 g, 35.80 mmol) in THF (33 ml) at room temperature was added 1-bromo-4-fluoro-2-methoxybenzene (3.13 mL, 24.39 mmol) and the reaction was stirred at 70 C for 1.5 hr. The reaction was then cooled to 0 C, and Fe(acac)3 (0.574 g, 1.63 mmol) was added. After 1 minute, allyl chloride (1.33 mL, 16.26 mmol) was added and the reaction was stirred at 0 C for 30 min. The mixture was warmed to room temperature over 1 hr and was heated at 70 C overnight. The reaction was cooled and diluted with petroleum ether (100 mL). The reaction was then quenched by the addition of a saturated NH4Cl solution (100 mL). The mixture was filtered through a Celite pad and the layers were separated. The aqueous layer was extracted with petroleum ether (2 x 100 mL) and the combined organic phases were dried over Na2SO4 and carefully concentrated (25 C, 250 mbar). The residue was purified by Isco chromatography (100% pet ether as the eleuent) to provide (E,Z)-4-fluoro-2- methoxy-1-(prop-1-en-1-yl)benzene (2.25 g, 83 % yield) as a colorless oil. This mixture was approximately a 3:1 mixture of E and Z isomers with a trace of the allyl isomer present. This material was used directly in the next step.1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J = 8.3, 6.8 Hz, 1H), 6.65- 6.53 (m, 3H), 6.14 (dq, J = 15.8, 6.6 Hz, 1H), 3.82 (s, 3H), 1.88 (dd, J = 6.6, 1.7 Hz, 3H).19F NMR (376 MHz, CDCl3) delta -113.30.

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; DOW AGROSCIENCES LLC; BUCHAN, Zachary A.; LU, Yu; JONES, David M.; MEYER, Kevin G.; YAO, Chenglin; (110 pag.)WO2018/44996; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, 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 887581-09-1, Application In Synthesis of (2-Bromo-5-methoxyphenyl)methanamine

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2-Bromo-5-methoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

4-Hydroxy phenyl acetic acid-t-butyl ester (Reagent E) A stirred suspension of 4-hydroxy-phenyl acetic acid (0.152 g, 1 mmol) in anhydrous toluene (5 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (1 mL, 4.17 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. The residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.11 g, 56%). 1H-NMR (300 MHz, CDCl3): delta1.44(s, 9H), 3.45(s, 2H), 6.55(s, 1H), 6.69(d, J=8.8 Hz, 2H), 7.06(d, J=8.5 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, Formula: C4H8Br2O

To a room temperature mixture of the [T-BUTYL-2- ( {4- [4- (2-] ethoxyethoxy) phenyl] phenyl) sulfonyl) acetate product (4) from Part C (800 mg, 1.9 mmol) in 8 mL DMF was added 18-crown-6 (150 mg, 0.6 mmol), potassium carbonate (1.3 g, 9.5 mmol), and bis (2-bromoethyl) ether (480 mg, 2.1 mmol). The mixture was stirred at room temperature for 18 hr. Subsequently, no starting material (4) was detectable by HPLC. The resulting mixture was concentrated, diluted in cold ether, and filtered to produce 800 mg (86% yield) of the desired compound (5). LCMS: [[M+NA] =] 513.2.

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; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
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Reference of 112970-44-2, The chemical industry reduces the impact on the environment during synthesis 112970-44-2, name is 2-Bromo-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

A solution of the bromoaniline (208 mmol) in 50% hydrochloric acid (40 mL) was added to a solution of trichloroacetaldehyde hydrate (312 mmol) and sodium sulfate (967 mmol) in water (450 mL) and the reaction mixture was maintained for 1 h. A solution of hydroxylamine hydrochloride (793 mmol) in water (240 mL) was added and the reaction mixture was heated at 60 C. for 2 h. The aqueous layer was decanted and the residual red oil, which solidifies upon standing, was purified by chromatography (6/6/1 petroleum ether/dichloromethane/ethyl acetate) to provide the alpha-oxime amide in 29% yield as a light yellow solid.

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-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok; US2007/78147; (2007); A1;,
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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 36805-97-7 as follows. Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

Step C: (2Z)-1-[2-(3-Bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-fluoro-2-propen-1-one; To a solution of 1-[2-(3-bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-2-fluoroethanone (10 mg, 0.025 mmol) in DMF (2 mL) was added DMF di-tert-butyl acetal (0.85 g, 4.2 mmol) and the reaction was heated at 80 C. for 15 min. The crude reaction mixture was adsorbed to silica gel and purified by LC (5-50% EtOAc in hexanes) to give the title compound (10 mg, 88%). ESIMS (M+H)+=456.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
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Electric Literature of 2674-34-2,Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 compound Q-9 (5.0 g, 16.77 mmol) in CH3CN (50 mL) was heated to 100 0C, followed by the addition of a solution of eerie ammonium nitrate (CAN, 14 g, 25.54 mmol) in water (75 mL) over a period of 30 min. The reaction mixture was then allowed to cool to room temperature and stirred for another 30 min. The resulting precipitate was filtered, washed with water (20 mL), and dried under high vacuum to furnish compound Q-10 (2.6 g, 58%) as a yellow solid. TLC Rf = 0.4 (petroleum ether – EtOAc, 9:1); MS (ES) mlz 266 (M – H)”.

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-Dibromo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; DJABALLAH, Hakim; ANTCZAK, Christophe; WO2010/129049; (2010); 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. 458-50-4, name is 4-Bromo-3-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluoroanisole

A mixture of tert-butyl ((3S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-(2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamido)-1H-indol-4-yl)pyrrolidin-3-yl)carbamate (50 mg, 0.072 mmol), 1-bromo-2-fluoro-4-methoxybenzene (22.3 mg, 0.109 mmol), copper(I) iodide (2.1 mg, 10.9 mumol) and potassium phosphate, tribasic (32.3 mg, 0.152 mmol) was purged with N2 and treated with N,N-dimethylcyclohexane-1,2-diamine (6.2 mg, 0.043 mmol) in 0.5 mL toluene. The reaction mixture was further treated with 0.3 mL DMF and heated to 110 C. for 40 hrs. After cooling to r.t., the reaction mixture was diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude product was dissolved in 1 mL THF and treated with 0.5 mL of TBAF solution (1.0 M in THF). The resulting mixture was stirred at r.t. for 1 hr, then diluted with water and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude was purified by flash chromatography (eluted with EtOAc) and the obtained product was then dissolved in 1 mL DCM and treated with 1 mL TFA. The resulting mixture was stirred at r.t. for 1 hr and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C32H31F2N6O4 (M+H)+: m/z=601.2; found 601.4.

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 458-50-4.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); 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. 21702-84-1, name is 2,4-Dibromo-1-methoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,4-Dibromo-1-methoxybenzene

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

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:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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Electric Literature of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Magnesium (172.4 mg; made by Wako Pure Chemical Industries Co., Ltd.), dehydrated THF (5 mL), dibromoethane (20 muL; made by Tokyo Chemical Industry Co., Ltd.), and 1-(benzyloxy)-3-bromobenzene-THF solution [15 mL; solution prepared by dissolving 1-(benzyloxy)-3-bromobenzene (1.3146 g; made by Tokyo Chemical Industry Co., Ltd.) in dehydrated THF (15 mL)] were added and stirred for one hour by reflux in a nitrogen atmosphere. The reaction solution was cooled to – 78C and bubbled for 20 minutes by SO2 gas. The reaction solution was brought to room temperature, bubbled for 10 minutes with nitrogen gas, and filtered. The filtrate was concentrated, and the residue obtained was dissolved in CH2Cl2 (25 mL), then cooled to 0C. SO2Cl2 (0.6 mL; made by Wako Pure Chemical Industries Co., Ltd.) was added to this solution and stirred overnight while warming to room temperature. Water was added to the reaction solution. After filtering by Celite, the filtrate was washed with brine. The organic layer was dried by anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The title compound was obtained as a crude product (1.3811 g). This crude product was used in the next reaction without any particular purification.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Kasei Pharma Corporation; EP2484668; (2012); A1;,
Ether – Wikipedia,
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