Category: ethers-buliding-blocks

103291-07-2, 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 103291-07-2 as follows.

To a solution of 5-bromo-2-fluoroanisole (1.00 g, 4.88 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (125 mg, 5.12 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After cooling to room temperature, 5-bromo-2-formylpyridine (1.09 g, 5.86 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 80 C overnight. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was used in the next step without further purification. C13H11BrFNO2; MW 312.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 103291-07-2, and friends who are interested can also refer to it.

Reference:
Article; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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54149-17-6, Adding some certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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 54149-17-6.

General procedure: DBU (4.5mmol) and 1-bromo-2-methoxyethane or 1-(2?-methoxyethoxy)-2-bromoethane were added to a solution of a triterpenic acid 1, 2, 3, 4 (2.2mmol) in the mixture of CH2Cl2 (6mL) and MeCN (2mL). The reaction mixture was stirred for 2 days at room temperature. The work-up (A), column chromatography on silica gel, and crystallization afforded final products 1a – 3a and 1b – 3b.

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 54149-17-6.

Reference:
Article; Eignerova, Barbara; Tichy, Michal; Krasulova, Jana; Kvasnica, Miroslav; Rarova, Lucie; Christova, Romana; Urban, Milan; Bednarczyk-Cwynar, Barbara; Hajduch, Marian; Sarek, Jan; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 403 – 420;,
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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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., 2062-98-8

EXAMPLE 11 EXAMPLE OF PRODUCTION OF COMPOUND (71a); Into a flask (internal capacity: 300 mL) under a nitrogen gas atmosphere, CH3COCH2OH (50.0 g), R-225 (81.6 g) and NaF (85.3 g) were put, and stirring was continued while the internal temperature of the flask was kept to be at most 10C. FCOCF(CF3)OCF2CF2CF3 (213.3 g) was dropwise added thereto over a period of two hours, and then the internal temperature of the flask was returned to 25C and stirring was carried out for 12 hours. Into a filtrate obtained by pressure filtration of a solution in the flask, a saturated sodium hydrogen carbonate aqueous solution (200 mL) was added to obtain a double layered solution. The organic layer was separated and washed with water (200 mL) and dehydrated with magnesium sulfate and then concentrated by an evaporator, to obtain a concentrate (230.7 g). In the concentrate, the following compound (71a) was contained, and a GC purity of the compound (71a) was 87.2%. The reaction was separately carried out under the same conditions, whereby a concentrate (96.0 g) having a GC purity of 96.5% was obtained. The concentrate obtained by the reaction twice was distilled under reduced pressure, and as a result, a fraction (281.3 g) of 67 to 71C/1.06 kPa (absolute pressure) was obtained. The fraction was analyzed by GC and NMR, and as a result, it was confirmed that the compound (71a) having a purity of 97.9% was formed. 1H-NMR (300.4 MHz, solvent: CDCl3, standard: TMS) delta (ppm): 2.21 (s, 3H), 4.91 (q, 16.5 Hz, 2H). 19F-NMR (282.6 MHz, solvent: CDCl3, standard: CFCl3) delta (ppm): -79.6 to -80.3 (1F), -81.7 to -81.8 (3F), -82.4 to -82.5 (3F), -86.5 to -87.0 (1F), -130.1 to -130.2 (2F), -132.8 (1F).

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; ASAHI GLASS COMPANY LTD.; EP1679311; (2006); A1;,
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74137-36-3, The chemical industry reduces the impact on the environment during synthesis 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Tris(dibenzylideneacetone)dipalladium(0) (6.53 g, 7.15 mmol) was added in one portion to a stirred solution of the bromide of Preparation 1 (38.0 g, 143 mmol), 1,1′-bis(diphenylphosphino)ferrocene (9.3 g, 16.8 mmol) and zinc cyanide (20.0 g, 172 mmol) in N,N-dimethylformamide (300 ml) at room temperature under nitrogen. The reaction was heated at 100¡ã C. for 14 hours and cooled to room temperature. Water (1500 ml) was added and the mixture was extracted with ethyl acetate (3.x.500 ml). The combined organics were filtered and the filtrate was washed with water (500 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene (1000 ml) to provide the title compound (18.0 g) as a tan solid. 1H-NMR (300 MHz, CDCl3): delta=3.83 (3H, s), 7.31 (2H, s), 7.48 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US2005/54707; (2005); A1;,
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74137-36-3, 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3,5-Dibromoanisole (15.57 g, 58.5 mmol) and tetrabutylammonium bromide (1.0 g, 3.1 mmol) were suspended in 48percent hydrobromic acid (100 mL) and refluxed for 3 days. After cooling to room temperature the reaction mixture was extracted with methylene chloride (3.x.60 mL). The combined organic layers were washed with water, dried over magnesium sulfate, and evaporated. The crude product was filtered over a pad of silica gel (ethyl acetate/heptane 10:1). After removal of the solvent, 14.23 g (97percent of 3,5-dibromophenol was obtained as pale brown needles.

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

Reference:
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
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60792-79-2, 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 60792-79-2 as follows.

Intermediate 20 6-(2-(2-Amino-ethoxyl-ethylamino(at)7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro- quinoline-3-carboxylic acid (A) and 7-f 2-(2-Amino-ethoxy)-ethylaminol-1-cyclouropyl-6-flnoro-4-oxo-1,4-dihydro (at)uinoIine- 3-carboxylic acid (B) To a solution of 7-chloro-l-eyelopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.55g, 1.95 mmol) in 1-methyl-2-pyrrolidone (40 mL) bis-(2-aminoethyl)-ether dihydrochloride (2.1g, 11.9 mmol, 6eq. ) and DBU (3.49 mL, 23.4 mmol, 12 eq. ) added and the reaction mixture was stirred at 110 C for 18 hours. The reaction mixture was then diluted with water (70 mL), pH was adjusted to 11 and extracted with CH2Cl2 (9×40 mL). Water layer was then acified with H2S04 to pH 6.8, extracted with 50 mL of CH2C12 and then evaporated in vacuum. Crude product was diluted in 2-propanol (60 mL), stirred at 82 C for 20 minutes and filtrated. Precipitate was pure salt (Na2S04). 2-Propanol was evaporated in vacuum and product was purified by column chromatography (fraction, eluent: CH2C12- MeOH-NH3-CH3CN=4:4:2:1) yielding 0.5g of title compounds as a mixture of chloro and fluoro derivatives in ratio 3:1 MS (ES+) m/z : [MH] + = 365.8 (A) (75 %) MS (ES+) m/z : [MH] (at) = 349.4 (B) (25 %)

According to the analysis of related databases, 2,2′-Oxybis(ethylamine) dihydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2005/108413; (2005); A1;,
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461-82-5, The chemical industry reduces the impact on the environment during synthesis 461-82-5, name is 4-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

A method for preparing 2,6-dibromo-4- (trifluoromethoxy) aniline,Including the following steps:The sodium sulfate was filtered off embodiment Example 4 156g crystallization mother liquor into 250mL 4-neck flask,Start stirring dropping 17.5 (0.175mol) sulfuric acid,Then, 36.5 g of sodium bromide (0.354 moL) was added and then 30 g (99percent, 0.168 mol) of 4-trifluoromethoxyaniline was added.Adjust the temperature to above 30 ,Start dropping 35percent hydrogen peroxide 38g,When dropping temperature rise,When the temperature rose to 50 ,By controlling the cooling liquid dripping temperature control between 50 ~ 55 ,Keep the temperature drops off,Drip finished insulation 3 hours,Cooling to about 30 ,filter,Filter cake drying,White crystals of 2,6-dibromo-4-trifluoromethoxyaniline 55.8 g, purity99.6percent (HPLC), yield 99.2percent.

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yancheng Limin Agrochemical Co., Ltd.; Huang Haijun; Zhu Mingliang; (7 pag.)CN106631839; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 1579-40-4, name is Di-p-tolyl Ether, 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 1579-40-4, 1579-40-4

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

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, Di-p-tolyl Ether, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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. 321-28-8.

The mixture of 2-chloro-5-nitrobenzoyl chloride (4.0 g, 18.18 mmol), 2-fluoroanisole (5.0 mL) and AlCl3 (3.63 g, 27.27 mmol) was stirred at room temperature for 24 h. The reaction mixture was poured into 10% HCl aqueous solution cooled in ice bath, which was extracted with EtOAc (100 mL ¡Á 3). The combined organic layer was washed with brine (100 mL ¡Á 1) and dried over anhydrous Na2SO4. The crude product was provided after evaporation and recrystalized with EtOAc to give compound 2b as white solid (5.40 g, 96%); mp 113-115 C; 1H NMR (DMSO-d6) delta (ppm): 8.41 (dd, J1 = 8.7 Hz, J2 = 2.4 Hz, 1H, ArH), 8.35 (d, J = 2.4 Hz, 1H, ArH), 7.88 (d, J = 8.7 Hz, 1H, ArH), 7.60-7.67 (m, 2H, ArH), 7.28 (t, J = 8.4 Hz, 1H, ArH), 4.01 (s, 3H, OCH3); HRMS (ESI): m/z, Calcd for C14H10ClFNO4 [M+H+]: 310.0277, Found 310.0297.

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

Reference:
Article; Liu, Chang; Jin, Jing; Chen, Liang; Zhou, Jie; Chen, Xiaoguang; Fu, Decai; Song, Hongrui; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2992 – 2999;,
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74137-36-3, The chemical industry reduces the impact on the environment during synthesis 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Step 2: Preparation of 1-bromo-3-ethylsulfanyl-5-methoxy-benzene To a mixture 1,3-dibromo-5-methoxy-benzene (2.65 g, 10 mmol) and sodium thioethoxide (1.01 g, 12 mmol) was added dimethylformamide (30 mL) at room temperature. Then, the resulting light yellow solution was heated to 105¡ã C. and stirred for 2 h at which time TLC analysis of the mixture indicated the absence of starting material. The reaction mixture was cooled to room temperature and diluted with water (50 mL) and brine solution (50 mL). Then, the organic compound was extracted into ethyl acetate (3*50 mL). The combined extracts were washed with brine solution (150 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and the concentration of the solution under reduced pressure gave the crude residue which was purified by using an ISCO 120 g column chromatography, eluding with 0-20percent ethyl actetate in hexanes to obtain 1-bromo-3-ethylsulfanyl-5-methoxy-benzene (1.35 g, 55percent) as a white solid: EI(+)-HRMS m/e calcd for C9H11BrOS (M)+ 245.9715, found 245.9713.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dominique, Romyr; Goodnow, JR., Robert Alan; Kowalczyk, Agnieszka; Lou, Jianping; Qiao, Qi; Siddurl, Achyutharao; Tilley, Jefferson Wright; US2009/227603; (2009); A1;,
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