Tag: M.W=200-300

Reference of 2674-34-2, 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 2674-34-2 as follows.

Into a 200-mL three-neck flask were put 8.9 g (30 mmol) of 1,4-dibromo-2,5-dimethoxybenzene, 10 g (72 mmol) of 2-fluorophenylboronic acid, 15 mL of toluene, 15 mL of diethylene glycol dimethyl ether (diglyme), and 60 mL of a sodium carbonate aqueous solution (2.0 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.69 g (0.60 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 2 hours. The mixture was cooled down to room temperature and degassed again under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. After the heating, 0.69 g (0.60 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to this mixture, and the mixture was heated at the same temperature for 5 hours. After the heating, 2.0 g (14 mmol) of 2-fluorophenylboronic acid was added to this mixture, and the mixture was further stirred at the same temperature for 3 hours. After the heating, the mixture was cooled down to the room temperature and degassed under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. This mixture was heated to 80 C., 0.64 g (0.55 mmol) of tetrakis(triphenylphosphine)palladium(0) and 3.0 g (21 mmol) of 2-fluorophenylboronic acid were added to the mixture, and the mixture was stirred at the same temperature for 2 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a compound. The obtained compound was recrystallized with toluene to give 2.5 g of a target. The compound obtained by the concentration of the filtrate was purified by column chromatography (a developing solvent: a mixed solvent of hexane and ethyl acetate in a ratio of 30:1) to give 0.3 g of a target. The targets were 2.8 g in total, and the yield was 29%. A synthesis scheme of the above synthesis method is shown in (A-1) below.

According to the analysis of related databases, 2674-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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Related Products of 156573-09-0, These common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, 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.

4-Formylphenylboronic acid (s47) (75.9 g),4-bromo-2,3-difluoroethoxybenzene (s48) (100.0 g), potassium phosphate (269.0g), dichlorobistriphenylphosphinepalladium (II) (Pd(Ph3P)2Cl2;8.9 g) and 1,4-dioxane (500 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 25 C, it was treated with water,and the aqueous layer was extracted with toluene. The combined organic layers were washed with water,and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder. The product was purified by recrystallization from a mixed solvent of heptane and toluene (heptane:toluene=l: 1 by volume) to give 4-ethoxy-4′-formyl-2,3-difluoro-l,l’-biphenyl (s49) (102.8g). The yield based on the compound (s48) was 92.9%.

The synthetic route of 156573-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; KOBAYASHI, MASAHIDE; (87 pag.)JP5849664; (2016); B2;,
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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. 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C15H13NO

General procedure: To a microwave vial, a mixture of 2-alkynylaniline (1 equiv), sulfonyl hydrazide (1.5 equiv), I2 (10 mol%) and pTSA (50 mol%) was taken in 1,4-dioxane irradiated for 15 min at 110C, 100W in CEM microwave synthesizer. The progress and completion of reaction is monitored by TLC using EtOAc/n-Hexane (1:10) as an eluent. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate. The combined organic phase was washed with sodium thiosulphate (50 mL) and dried over Na2SO4. After filtration and evaporation of the solvents in vacuum, the mixture of products was separated by column chromatography on silica gel (EtOAc/n-hexane: 1:10) to yield the desired product 3.

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; Sharma, Shivani; Pathare, Ramdas S.; Sukanya; Maurya, Antim K.; Goswami, Bhagyashree; Agnihotri, Vijai K.; Sawant, Devesh M.; Pardasani, Ram T.; Tetrahedron Letters; vol. 58; 40; (2017); p. 3823 – 3826;,
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Related Products of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-methoxyaniline, molecular formula is C7H8BrNO, 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 : Synthesis of N-(3-Bromo-5-methoxy-phenyl)acetamideTo a solution of 20 g of 3-bromo-5-methoxy-aniline in 200 mL DCM was added 27.44 mL triethylamine at 0 C .To the reaction mixture was added 7.06 mL acetyl chloride dropwise over 30 min. The reaction was stirred at 30C for 3 h, and then poured onto ice. The pH was adjusted to pH 7 with aqueous NaHC03 and the precipitated solids were removed by filtration. The aqueous was extracted with DCM and the combined organic extracts were dried over sodium sulfate, filtered and evaporated under reduced pressure to yield 20 g N-(3-bromo-5- methoxy-phenyl) acetamide as solid.Analysis: HPLC-MS: Rt = 2.44 min (method Q), M+H = 244 / 246

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); 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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

Step 1:Magnesium (8.24 g, 0.339 mol) was added to 300 mL of tetrahydrofuran (THF) in a reactor substituted with nitrogen atmosphere and dissolved by stirring. While keeping the internal temperature at 20 to 30 C, 4-bromophenetol 62 g, 0.308 mol) and 220 mL of tetrahydrofuran was slowly added thereto. After completion of the addition, the internal temperature was raised to 40 to 45 C and stirred for 2 hours. Step 2: In a reactor substituted with nitrogen atmosphere, (S)-tert-butyl 2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)aziridine-1-carboxylate (50 g, 0.206 mol) was added to 50 mL of toluene and dissolved with stirring, and CuBrS(CH3)2 (0.4 g, 0.002 mol) was added thereto. The internal temperature was further stirred for 30 minutes while maintaining the internal temperature at 20 to 25 C,and the internal temperature was cooled to -40 C.The solution of 4-bromophenetol magnesium bromide prepared according to the above step 1 was slowly added while keeping the internal temperature at -40 C or lower.After completion of the addition, the internal temperature was raised to -30 to -20 C and stirred for 1 hour. When the reaction was complete, 400 mL of 10% acetic acid aqueous solution and 400 mL of toluene were added to quench and separate.The separated oil layer was washed with 400 mL of a 7% sodium Sodium bicarbonate aqueous solution and 400 mL of purified water, and Sodium sulfate was added to dehydrate and then filtered.Thereafter, the filtrate was concentrated, 150 mL of methanol was added to the concentrated residue, stirred at an internal temperature of 20 to 25 C for 1 hour, and then filtered. The filtrate was concentrated again to give 75.1 g of the title compound tert-butyl (1S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-ethoxyphenyl)ethylcarbamate yield: 100 %

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eseuti Pam Co., Ltd.; Kim Yeong-hun; Oh Jun-hyeon; Kang Sang-gyu; Jang Sun-gi; Im Geun-jo; (14 pag.)KR2018/50091; (2018); A;,
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Application of 1663-61-2, 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. 1663-61-2, name is (Triethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Method B (microwave irradiation) – The reaction mixture composed of cinnamic acid hydrazide 2 (0.50 g, 3.0 mmol), triethyl orthoester (6.0 mmol) and 2 mL of glacial AcOH was placed into 10 mL crimp-sealed thick-walled glass tube. The reaction vessel was placed in CEM Discover microwave-enhanced synthesis system operating at 125 +/- 5 C, power 250 W and kept for 10 min. After cooling, the excessive orthoester and AcOH were evaporated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:5, v/v.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Tetrahedron Letters; vol. 53; 1; (2012); p. 76 – 77;,
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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: 1-Bromo-4-fluoro-2-methoxybenzene

A solution of dry diisopropylamine (10 g, 99 mmol) in dry THFunder nitrogen was cooled with a -78 C bath, n-butyl lithium (2.50 M in hexane, 40 mL, 99 mmol) was added andthe solution was stirred at -78 C for 20 minutes. 1-Bromo-4-fluoro-2-methoxybenzene (17.0 g, 82.5 mmol) wasadded. After stirring at -78 C for 2 hours, the solution was bubbled with CO2 and then warmed to 0 C. Then 1 NHCl was added until pH=3-4 and the mixtue was extracted with AcOEt. The combined organic layers were washedwith brine, dried over anhydrous sodium sulphate and concentrated to afford 3-bromo-6-fluoro-2-methoxybenzoicacid.

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

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; (128 pag.)EP2744499; (2016); B1;,
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Synthetic Route of 36942-56-0, 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. 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.5M nBuLi (1.8 mL, 4.5 mmol) was added dropwise over 5 minutes into a mixture of 2-bromo-4-methoxy-1-methylbenzene (750 mg, 3.73 mmol) in anhydrous THF (30 mL) at -78 C. After the mixture was stirred at -78 C. for 20 minutes, anhydrous trimethyl borate (0.62 g, 6 mmol) was added into the solution at -78 C. The reaction mixture was brought to room temperature for over period of 2 h. The reaction was quenched by 2N HCl (1 mL). The THF was removed by vacuum. The crude product was diluted with 2N HCl (100 mL). The acidic solution was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate fraction was dried over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed by vacuum to yield a pale yellow solid (0.43 g, 69%).

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; TargeGen, Inc.; US2005/245524; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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 6358-77-6, HPLC of Formula: C7H8BrNO

To a stirred 100 mL RBF was added 5-bromo-2-methoxyaniline (7 g, 34.6 mmol) and DIEA (12.05 mL, 69.3 mmol) in DCM (100 mL). At 0 C, furan-2-carbonyl chloride (3.41 mL, 34.6 mmol) was added dropwise. The reaction mixture was stirred at 0 C and allowed to warm to RT overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo. The sample was preloaded on silica and purified with flash chromatography on a CombiFlash silica gel column (80 g, Teledyne Isco, gradient 20% EtOAc in hexanes) to give Example 209.1. LCMS (ESI) m/z= 297 [M+Hf?.

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

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Application of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5-bromo-2-(trifluoromethoxy)aniline (2 g, 7.8 mmol), K2CO3 (2.7 g, 19.5 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (50% in THF, 4.4 mL, 15.6 mmol) in dioxane (60 mL) was degassed for 20 min with N2. PdCl2(dppf)- CH2Cl2 (319 mg, 0.39 mmol) was added and the mixture was further degassed for 10 min then heated to 100 oC for 1 h. The reaction mixture was cooled to rt, filtered through a pad of celite, concentrated, and purified by chromatography (EA/hexane) to provide 1.49 g (74%) of Intermediate 44A. LCMS [m/z] calculated for C8H8F3NO: 191.1 found 192.2[M+H]+, tR=4.22 min (Method 4).

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; YEAGER, Adam; TURNBULL, Philip; ZHANG, Lin; FAN, Junhua; TAMIYA, Junko; STEINBERG, Marcos; FOWLER, Tom; BENELKEBIR, Hanae; PASCERI, Raffaele; IEVA, Maria; GRANT, Kevan; TRAN, Yang; (403 pag.)WO2018/45246; (2018); A1;,
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