Tag: M.W=200-300

Reference of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
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Synthetic Route of 450-88-4,Some common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-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.

Reference Example 29 (1) In 15 ml of N, N-dimethylformamide were dissolved 3.94 g of [2-BROMO-5-FLUOROPHENOL] and 1.62 ml of methyl iodide, slowly added thereto was 5.08 g of potassium carbonate under ice-cooling. The mixture was stirred at room temperature for 3 hours. After insoluble matters were removed by filtration, distilled water was added to the filtrate, and the mixture was extracted with diethyl ether and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography- (hexane : ethyl acetate=19: [1-9] : 1), to give 4.10 g of [1-BROMO4-FLUORO-2-] methoxybenzene. MS (m/z): 204/206 [(M++L) O] (2) To 7 ml of tetrahydrofuran were added 486 mg of magnesium and trace of iodine, and dropped thereto was a solution of 4.10 g of the compound of the above [(1)] in 16 ml of tetrahydrofuran, to prepare Grignard reagent. To the solution, a solution of 1.96 g of 4-methoxypyridine in 7 ml of tetrahydrofuran was added dropwise under nitrogen atmosphere [AT-60C] or below. Subsequently, a solution of 3.75 g of benzyl chloroformate in 18 ml of tetrahydrofuran was added dropwise, and the mixture was stirred for 3 hours. The temperature of the mixture was raised to room temperature, and 40 ml of a 5% aqueous citric acid solution was added thereto. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=2: [1-1] : 2), to give 3.15 g of [1-BENZYLOXYCARBONYL-2- (4-FLUORO-2-METHOXYPHENYL)-4-OXO-] 3,4-dihydro-2H-pyridine. MS (m/z): 356 [[M++1]] (3) In a mixed solution of 79 ml of ethanol and 6 ml of tetrahydrofuran was dissolved 3.15 g of the compound of the above (2), and added thereto was 706 mg of sodium borohydride and the mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated and distilled water was added to the residue. The mixture was extracted with chloroform, and the organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform: acetone=19: [1-9] : 1), to give 1.62 g of [1-BENZYLOXYCARBONYL-2- (4-FLUORO-2-] methoxyphenyl)-4-hydroxypiperidine. MS (m/z): 360 [[M++1]] (4) In 20 ml of toluene was dissolved 1.62 g of the compound of the above (3), added thereto was 876 mg of 1, [1′-] carbonyldiimidazole and the mixture was stirred at [60C] for an hour. Added thereto was 1.09 ml of ethanolamine, and the mixture was stirred at [60C] for 6 hours. To the reaction mixture was added distilled water and the mixture was extracted with chloroform. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (chloroform: acetone=4: [1-1] : 1), to give 1.81 g of [1-BENZYLOXYCARBONYL-2- (4-FLUORO-2-METHOXYPHENYL)-4- (2-] hydroxyethylaminocarbonyloxy) piperidine. MS (m/z): 447 [[M++L]] [(5)] In 20 ml of methanol was dissolved 1.81 g of the compound of the above (4), and added thereto was 90 mg of 10% palladium-carbon, and the mixture was stirred at room temperature for an hour under hydrogen atmosphere. After insoluble matters were removed by filtration, the filtrate was concentrated. To the residue was added diethyl ether and precipitates were collected by filtration, to give 1.30 g of [2- (4-FLUORO 2-METHOXYPHENYL)-4- (2-] hydroxyethylaminocarbonyloxy) piperidine as shown in Table 134 below.

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-fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; WO2003/99787; (2003); 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., name: 4-Bromo-3-methoxyaniline

2-(2-chlorophenylaminoacetic acid (lSOmg. 808 imoD and 4-bromo-3-methoxyaniline (171 mg, 849 imol) were combined with dichloromethane (10 m). At 0¡ãC N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (163 mg, 849 imol) was added. The reaction mixture was stirred at O ¡ãC for 30 mm, then at RT oyernight. The mixture was poured on water (20 ml) and extracted with dichloromethane (3 x 15 ml). chromatography (silicagel, ethyl acetate / heptane = 20:80 to 50:50) yielded N-(4-bromo-3-methoxyphenyl)-2-(2- chlorophenylamino)acetamide (225 mg, 75percent) as yellow solid. MS: mle =371.1 [M+H].

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECCARELLI, Simona M.; JAGASIA, Ravi; JAKOB-ROETNE, Roland; PETERS, Jens-Uwe; WICHMANN, Juergen; WO2014/79850; (2014); A1;,
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Synthetic Route of 60876-70-2, 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. 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

[3-(4-Benzyloxy)phenoxy]benzo[b]thiophene-2-boronic acid was reacted with 4-(-tertbutoxy)bromobenzene according to the conditions described above for [2-iodo-3-(4-benzyloxy)phenoxy]benzo[b]thiophene and 4-(tertbutoxy)phenyl boronic acid to give [2-(4-tertbutyloxyphenyl)-3-(4-benzyloxy)phenoxy]benzo[b]thiophene in 81% yield.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(tert-butoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; US5488058; (1996); A;,
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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. 588-96-5, name is p-Bromophenetole, A new synthetic method of this compound is introduced below., Recommanded Product: p-Bromophenetole

(1) A small amount of iodine was added to a suspension of 1-bromo-4-ethoxybenzene (484 muL) and magnesium (82.3 mg) in THF at room temperature in a nitrogen atmosphere, and the mixture was stirred at 50 C. for one hour. The reaction solution was returned to room temperature and a solution of 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde (300 mg) in tetrahydrofuran (1 mL) was added, followed by stirring at 50 C. for one hour. Tetrahydrofuran was concentrated under reduced pressure and a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was filtered through diatomaceous earth, and then the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1?9:1) to give (5-cyclopropyl-6-methoxypyridin-2-yl)(4-ethoxyphenyl)methanol as a yellow oil (438 mg, 86%).

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; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
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Related Products of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-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.

15 g of 1-bromo-4-fluoro-2-methoxybenzene obtained by Production example 89 was dissolved in 150 mL of 1-methyl-2-pyrrolidone, added with 9.9 g of copper cyanide (I), and stirred at 180C for 5 hours. After allowing to cool, the reaction solution was poured into 500 mL of 14% ammonia aqueous solution, stirred for 45minutes, then added with 150 mL of diethyl ether, and stirred for another 10 minutes. After filtering off the insoluble substances through Celite, the solution was extracted with diethyl ether. The organic layer was washed with diluted aqueous ammonia, 5N hydrochloric acid, water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, to afford 10.1 g of the title compound as white crystals.1H-NMR ( 400 MHz, CDCl3 ) delta 3.93 ( 3H, s ), 6.67 – 6.74 ( 2H, m ), 7.54 ( 1H, dd, J = 6.0, 8.4 Hz )

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

Reference:
Patent; Eisai Co., Ltd.; EP1510516; (2005); 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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101-55-3

4-Bromodiphenyl ether (X = Br) (3.74 g, 15 mmol) was dissolved in 1,4-dioxane (50 ml)Addition of pinacol diboronate(4.52 g, 18 mmol),Potassium acetate (1.78 g, 18 mmol).Then, the catalyst [1,1′-bis (diphenylPhosphine) ferrocene] palladium dichloride [Pd (dppf) 2Cl2] (1.5 mmol, 1.11 g).With stirring, heated to 100 C, the reaction 5h (TLCDetection of raw materials disappear).Then, Intermediate (14) (4.44 g, 10 mmol) was added, and the reaction was maintained at 100 C for 22 hours14 disappears).Then, after distilling off the organic solvent, Intermediate (9) (yellow solid, 3.41 g, yield 70%, chemical purity and optical purity> = 99%) was obtained.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Liu Guobin; (12 pag.)CN104557945; (2017); B;,
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Application of 261762-35-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 261762-35-0 name is 5-Bromo-1,2-difluoro-3-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 20 N-( 1 -(7-chloro-4,5 -difluoro- 1 -hydroxy- 1 ,3-dihydrobenzo[cl [ 1 ,2″|oxaborol-6-yloxy”)-2-cva nopropan-2-yl)-4-(trifluoromethoxy)benzamide To a solution of 5-bromo-l,2-difluoro-3-methoxybenzene (8.9 g, 39.9 mmol) in THF (200 mL), LDA (17.6 mL, 43.9 mmol) is added dropwise at -78C and the mixture is stirred at the same temperature for 2 h. DMF (9.6 g, 131.7 mmol) is added at -78 C, and the mixture is stirred at -78C for 4 h. The reaction is quenched with saturated aq. NH4C1, extracted with EA, dried over Na2S04, and recrystallized to afford the desired product as a white solid (6 g, yield 60 %). :H NMR (400 MHz, CDC13): delta 10.20 (s, IH), 7.04-7.06 (m, 1H), 3.99 (s, 3H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-difluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; ANACOR PHARMACEUTICALS INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; PLATTNER, Jacob J.; PULLEY, Shon Roland; WHITE, William Hunter; ZHANG, Yong-Kang; ZHOU, Yasheen; WO2014/149793; (2014); A1;,
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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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(2-Bromoethoxy)-4-fluorobenzene

EXAMPLE 113 4-(3-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR149 From a mixture of 4-(3-fluorobenzyl)piperidine hydrochloride (500 mg, 2.18 mmol), 2-(4-fluorophenoxy)ethyl bromide (501 mg, 2.29 mmol) and K2 CO3 (615 mg, 4.45 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (360 mg, 81%): mp 155-157 C., 1 H NMR (CDCl3) 1.65-1.90 (m, 3H), 1.98-2.16 (m, 2H), 2.62 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.53 (m, 2H), 3.67 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-7.10 (m, 7H), 7.19-2.28 (m, 1H), 12.64 (bs, 1H); Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.35; H, 6.58; N, 3.77.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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Related Products of 36449-75-9, 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 25-mL round-bottom flask, were introduced compound 4.7 (450 mg, 1.25 mmol, 1.00 equiv), l-(2-bromoethyl)-2-methoxybenzene (400 mg, 1.86 mmol, 1.50 equiv), N,N-dimethylformamide (4 mL) and K2CO3 (260 mg, 1.87 mmol, 1.50 equiv). Reaction was stirred for 10 h at 80C and then quenched by the addition of 5 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The crude was purified by re-crystallization from ethyl ether to provide 450 mg (73%) of compound 4.8 as an off-white solid.

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

Reference:
Patent; NIMBUS APOLLO, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BORG, George; MASSE, Craig E.; WO2014/182943; (2014); A1;,
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