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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Product Details of 5905-69-1

Step 4) 1-difluoromethoxy-4-{3-[3-(2-fluoro-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (349 mg, 0.973 mmol) was dissolved in THF (2 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (2 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (300 mg 1.30 mmol), copper iodide (35 mg, 0.131 mmol), tetrakis(triphenylphosphine)palladium (70 mg, 0.060 mmol) and triethylamine (4.3 g, 42.5 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%, then 5% EtOAc in hexanes) afforded an oil 178 mg (53%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68-1.80 (m, 2H) 1.85-2.11 (m, 2H) 2.17-2.36 (m, 2H) 2.38-2.43 (m, 1H) 3.28-3.65 (m, 1H) 4.24-4.52 (m, 2H) 7.01-7.47 (m, 5H) 7.18 (d, J=8.8 Hz, 2H) 7.58 (d, J=8.8 Hz, 2H).

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; WYETH; US2009/48320; (2009); 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11BrO

General procedure: To a stirred solution of 1-(2-pyridyl)-b-carboline (0.245 g,1 mmol) in 10 mL DMF, sodium hydride (50% in mineral oil, 0.048 g,1 mmol) and bromo-hydrocarbon (1 mmol) was added. The reactionmixturewas stirred at room temperature for 1 h. After reactionwas finished, the mixture was poured into ice water and extractedwith ethyl acetate. The organic layer was washed with water anddried. Removal of the solvent gave the crude product that waspurified by silica gel column (dichloromethane: methanol 100:1 as the eluent). The solvent was removed and the product wasobtained.

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 1462-37-9.

Reference:
Article; Lu, Xing; Liu, Yan-Cheng; Orvig; Liang, Hong; Chen, Zhen-Feng; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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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. 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. Quality Control of 5-Bromo-2-(trifluoromethoxy)aniline

240 g (0.937 mol) of 5-bromo-2-(trifluoromethoxy)aniline were dissolved in 2400 mL of anh toluene. 112 mL (1.406 mol) of chloroacetyl chloride were added. It was stirred for 2 h at 100 C. The reaction mixture was concentrated on the rotavap. The residue was treated with 600 mL of cyclopentyl methyl ether and concentrated again. This procedure was performed twice yielding 324 g of the title compound. 1H-NM (400MHz, DMSO-d6): delta [ppm]= 4.39 (s, 2H), 7.40 – 7.44 (m, 1H), 7.49 (dd, 1H), 8.20 (d, 1H), 10.23 (s, 1H). LC-MS (Method 4): Rt = 1.27 min; MS (ESIpos): m/z = 332 [M+H]+.

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William J.; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; GEISLER, Jens; WO2015/140196; (2015); A1;,
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Related Products of 887581-09-1,Some common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, molecular formula is C8H10BrNO, 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: To a magnetically stirred solution of the formyl ester 8a (400 mg, 1.6 mmol) in CH2ClCH2Cl (5 mL) at room temperature, were added sequentially 2-bromobenzyl amine 3a (420 mg, 2.2 mmol) and AcOH (0.14 mL, 2.4 mmol) followed by refluxing of the mixture for 12 h. After cooling, the reaction mixture was treated with aqueous NaHCO3 solution and extracted with ethyl acetate (3 ¡Á 12 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Concentration of the filtrate followed by flash chromatography (ethyl acetate/hexane, 1:6 to 2:3) furnished the cyclic enamide 9aa (480 mg, 80%) as brown viscous oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Bromo-5-methoxyphenyl)methanamine, its application will become more common.

Reference:
Article; Satyanarayana, Gedu; Maier, Martin E.; Tetrahedron; vol. 68; 6; (2012); p. 1745 – 1749;,
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Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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.

To a solution of 3-bromo-5-fluoroanisole (250 mg, 1.22 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (32 mg, 1.28 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After cooling down to room temperature, 6-bromopyridin-2-yl carboxaldehyde (271 mg, 1.47 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 purified by column chromatography (hexane/ethyl acetate 8:2) to afford the analytically pure compound in 21% yield (80 mg). C13H11BrFNO2; MW 312; 1H NMR (acetone-d6): delta 7.74 (t, J = 7.6 Hz, 1H), 7.64-7.61 (m, 1H), 7.47 (dd, J = 0.9 Hz, J = 7.2 Hz, 1H), 6.92-6.90 (m, 1H), 6.81 (ddd, J = 0.6 Hz, J = 1.3 Hz, J = 9.1 Hz, 1H), 6.59 (dt, J = 2.5 Hz, J = 10.7 Hz, 1H), 5.77 (d, J = 4.7 Hz, 1H), 5.35 (d, J = 4.7 Hz, 1H), 3.79 (s, 3H); 13C NMR (acetone-d6): delta 165.8, 165.3, 140.8, 127.5, 120.3, 109.4, 106.1, 105.9, 101.0, 100.8, 75.8, 56.0; LC/MS m/z: 312-314 (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-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.

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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These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-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. COA of Formula: C15H23BrO

Production Example 7 of Optically Active AminoalcoholA 300 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.99 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 25.30 g of 4-methoxy-3,5-di-tert-butylbromobenzene and 119.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10 C., 1.45 g of L-alanine methyl ester hydrochloride was added. The temperature of the resulting mixture was raised to room temperature, and the mixture was further refluxed for 3 hours. The resulting reaction mixture was cooled to 0 to 5 C. To the reaction mixture were added dropwise 70.0 mL of an aqueous saturated ammonium chloride solution, and further 20.0 mL of water. The resulting mixture was stirred at 20 C. for 12 minutes. The resulting mixture was extracted with 70.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9830/70) to obtain 3.32 g of a pale yellow solid of (S)-2-amino-1,1-di(4-methoxy-3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.49 (2H, s), 7.34 (2H, s), 4.01 (1H, m), 3.86 (1H, brs), 3.67 (3H, s), 3.66 (3H, s), 1.44 (18H, s), 1.42 (18H, s), 1.22 (2H, br.s), 0.94 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 158.58, 158.29, 143.46, 142.94, 141.10, 139.19, 124.95, 124.84, 79.58, 64.76, 53, 42, 36.58, 36.50, 32.91, 21.75, 18.07

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

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
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Related Products of 589-10-6, These common heterocyclic compound, 589-10-6, name is (2-Bromoethoxy)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.

EXAMPLE 2; PREPARATION OF 4-CHLORO-5-METHOXY-2-(2-PHENOXYETHYL)INDAN-l-ONE; 4-Chloro-5-methoxyindan-l-one (14.0 kg, 71.2 mol) (Example 1) was slurried in n- heptane (154 L). Glacial acetic acid (2.14 kg, 35.6 mol) was then added followed by 1,1- dimethylhydrazine (6.42 kg, 106.8 mol) such that the temperature remained <40C. The batch was then heated to 900C for 3 h. The batch was cooled to 600C, treated with THF (28 L) then concentrated to 40 L by distillation under atmospheric pressure. The resulting concentrate was cooled to 500C and diluted with THF (182 L). The THF solution was held overnight at <15C. The batch was cooled to -500C by direct injection of liquid N2, then n-hexyllithium (2.39 M in hexane, 21.2 kg, 71.2 mol) was added over 1.5 h, maintaining the internal temperature <-25C. The resulting slurry was aged between -30 and -200C for 30 min then a solution of beta-bromophenetole (14.4 kg) in THF (14 L) was added over 5 min, maintaining the internal temperature <-25C. The batch was then aged at -50C for 30 min. 6 N HCl (30 kg 37% HCl + 30 kg H2O) was charged to the mixture which was then aged at 500C until complete hydrolysis of the intermediate hydrazone was confirmed by HPLC (1.5 h). After cooling the batch to 200C, isopropyl acetate (56 L) was added and the aqueous layer was discarded. The organic phase was washed with water (75 L) then concentrated to 40 L using vacuum distillation at 4O0C. n-Heptane (40 L) was added and after aging for 30 min at 400C, 0.2% seed of the product ketone was added. The mixture was stirred for 1 h to allow a seed bed to develop, then a further 80 L of n-heptane was charged over 1 h at 400C. The resulting slurry was allowed to cool to 200C overnight then cooled to 5C over 1 h before filtering. The filter cake was washed with 4:1 heptanerisopropyl acetate (25 L), then sucked dry under a stream OfN2 for 3 h. The solid was dried in a vacuum oven at 45C for 48 h affording 20.2 kg of product as an off white solid in 88% yield. 1H NMR (400 MHz, CDCl3) delta 7.70 (IH, d, J = 8.4 Hz), 7.35-7.25 (2H, m), 7.04-6.88 (4H, m), 4.25-4.15 (2H, m), 4.00 (3H, s), 3.46-3.35 (IH, m)> 2.98-2.87 (2H, m), 2.54- 2.41 (IH, m), 2.03-1.89 (IH, m); 13C NMR (IOO MHz, CDCl3) delta 206J, 160.2, 158.8, 153.2, 130.8, 129.5, 123.6, 120.8, 119.7, 1 14.5, 111.6, 65.9, 56.8, 45.0, 32.2 <>31.0.

The synthetic route of 589-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2007/81895; (2007); A2;,
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Synthetic Route of 6876-00-2, 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 6876-00-2 as follows.

EXAMPLE 25 1-(4-Chlorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane A Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.33 g) in dry tetrahydrofuran (2 ml) and magnesium (30 mg) under nitrogen using iodine as an initiator at ca 40 C for 50 min, was cooled to room temperature then treated with cuprous bromide (ca 20 mg) for 10 min. After cooling to -78 C., a solution of 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropane (Example 17) (0.32 g) in tetrahydrofuran was added slowly with stirring, then the mixture was allowed to warm to room temperature overnight. The mixture was treated with water (4 ml), then extracted with diethyl ether (3*20 ml). The combined organic extracts were washed with water (2*10 ml), dried, and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(4-chlorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (98 mg, 22%).

According to the analysis of related databases, 6876-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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These common heterocyclic compound, 38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, 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. Quality Control of 1-Bromo-4-cyclopropoxybenzene

Step 1: A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for2 hours. The solution was quenched with NH4CI (aq. lmL) at-78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 x 15 mL). The organic layer was dried with anhydrous Na2504, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 mm (method 2), m/z = 162.8 [M +H].

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

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 36449-75-9

General procedure: To a DMF solution (3 mL) of bromide derivative, were added sodium iodide (0.05 eq) and sodium azide (1.2 eq) at 40 C. The reaction mixture was stirred for overnight. Et2O (20 mL) was added to the mixture then the organic layer was washed with water (3 ¡Á 20 mL), dried over MgSO4 and concentrated under reduced pressure to give the azide derivative. Spectroscopic data of compounds are identical to those previously reported [10].

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

Reference:
Article; Menendez, Christophe; Chollet, Aurelien; Rodriguez, Frederic; Inard, Cyril; Pasca, Maria Rosalia; Lherbet, Christian; Baltas, Michel; European Journal of Medicinal Chemistry; vol. 52; (2012); p. 275 – 283;,
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