Tag: M.W=200-300

Some common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, molecular formula is C8H9BrO, 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. Formula: C8H9BrO

General procedure: A mixture of 17 (200 mg, 0.369 mmol), 2-bromo-1-methoxy-3-methylbenzene(148 mg, 0.737 mmol), Pd(OAc)2 (8.3 mg, 0.037 mmol), 2-dicyclohexylphosphino-2?,6?-di-isopropoxy-1,1?-biphenyl (34.4 mg,0.074 mmol), and Cs2CO3 (360 mg, 1.11 mmol) in toluene (7.5 ml) and water (1.5 ml) was stirred at 80 C for 25 h. Then, water was added tothe reaction mixture, and the product was extracted with AcOEt. Theorganic layer was successively washed with water and brine, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (hexane/AcOEt=40/60 to 10/90) to give the title compound as a white solid (43 mg, 21%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38197-43-2, its application will become more common.

Reference:
Article; Murafuji, Hidenobu; Sugawara, Hajime; Goto, Megumi; Oyama, Yoshiaki; Sakai, Hiroki; Imajo, Seiichi; Tomoo, Toshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3639 – 3653;,
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Related Products of 887268-25-9, 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. 887268-25-9, name is 2-Bromo-4-methyl-1-(trifluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-Bromo-5-methyl-2-trifluoromethoxybenzene (1.0 g, 3.92 mmol), bis(pinacolato)diboron (1.49 g, 5.88 mmol), potassium acetate (1.54 g, 15.7 mmol) and 1 ,1′-[bis(diphenylphosphino)ferrocene] dichloropalladium (II) (0.287 g, 0.392 mmol) were combined and stirred in dimethylsulphoxide (25 ml). The reaction flask was purged with nitrogen for 5 minutes before heating to 1000C for 10 hours. The mixture was cooled and partitioned between f¡ãrt-butylmethyl ether (100 ml) and water (100 ml). Insoluble material was removed by filtration then the organic extract dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford the crude title compound as a brown oil (895 mg, 76%). Material was taken on without further purification to next stage.

The synthetic route of 2-Bromo-4-methyl-1-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H12FNO

To a stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (33.7 g, 155.3mmol), 1-(4-fluoro-phenylcarbamoyl)-cyclopropane carboxylic acid (38.13 g, 170.8mmol) and anhydrous DCM (600 ml) was added EDCI (44.7 g, 233.9mmol) in portions. After stirring at r.t. for 1 h, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1st crop of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2nd crop of product. The combined yield of Cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl)-amide(4-fluoro-phenyl)-amide 64.5 g, yield: 98%. 1H-NMR (300MHz, CDCl3) delta: 8.9 (m, 2H), 7.35-7.18 (m, 8H), 6.95-6.85 (m, 4H), 5.03 (s,2H), 1.53(s, 2H).

According to the analysis of related databases, 168268-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jieming; Gu, Weijie; Bi, Xinzhou; Li, Huilan; Liao, Chen; Liu, Chunxia; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6674 – 6679;,
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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 18800-30-1 as follows. Formula: C8H8Br2O

To a solution of 1-bromo-4-(2-bromoethoxy)benzene (6, 1 g, 3.57 mmol), and 4-chloro-1H-pyrazole (439 mg, 4.2 mmol),, K2CO3 (985 mg, 7.14 mmol) and KI (29 mg, 0.17 mmol) were added and then heated at 80 C for 16 h. After completion, water (15 ml) was added into reaction mixture and the aqueous layer was extracted with ethyl acetate (2x15ml). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give 1-(2-(4-bromophenoxy)ethyl)-4-chloro-1H-pyrazole (7, 1.03 g, 83%) as white solid. 1H-NMR (400 MHz; CDCl3): d 4.26 (t, J = 5.0 Hz , 2H), 4.44 (t, J = 5.1 Hz , 2H), 6.74 (d, J = 8.9 Hz, 2H), 7.36 (d, J = 8.9 Hz, 2H), 7.44 (s, 1H), 7.51 (s, 1H).

According to the analysis of related databases, 18800-30-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; O’Brien, Alistair; Andrews, Stephen P.; Baig, Asma H.; Bortolato, Andrea; Brown, Alastair J.H.; Brown, Giles A.; Brown, Sue H.; Christopher, John A.; Congreve, Miles; Cooke, Robert M.; De Graaf, Chris; Errey, James C.; Fieldhouse, Charlotte; Jazayeri, Ali; Marshall, Fiona H.; Mason, Jonathan S.; Mobarec, Juan Carlos; Okrasa, Krzysztof; Steele, Kelly N.; Southall, Stacey M.; Teobald, Iryna; Watson, Steve P.; Weir, Malcolm; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
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Synthetic Route of 1515-89-5, A common heterocyclic compound, 1515-89-5, name is 1-Bromo-3-(methoxymethyl)benzene, molecular formula is C8H9BrO, 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.

PREPARATION 103 3-Methoxymethylphenylboronic Acid Obtained as a yellow solid (100%), from 1-bromo-3-methoxymethylbenzene (J. Amer. Chem. Soc., 1989, 111, 6311; Tetrahedron 1985, 41, 1435) and trimethyl borate1 using the procedure of Preparation 101. delta(DMSOd6): 3.27 (s,3H), 4.38 (s,2H), 7.31 (m,2H), 7.68 (m,2H), 7.98 (brs,2H).

The synthetic route of 1515-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer INC; US6387931; (2002); B1;,
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Synthetic Route of 53087-13-1, A common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (1 .29 g, 52.8 mmol) in dry THF (50 ml_). The mixture was refluxed and about 5% of a solution of 3- bromophenol (13.9 g, 52.8 mmol) was added. When the reaction had started, the solution of the bromide was added drop-wise and the mixture was then refluxed for one more hour. The mixture was cooled down to about 5 C and a solution of the cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added drop-wise. The mixture was stirred at rt for 72 h, then the reactio was quenched with cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2S04), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

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; MEDIVIR AB; BETHEL, Richard; ENEROTH, Anders; KLASSON, Bjoern; OeBERG, Fredrik; (73 pag.)WO2016/30335; (2016); A1;,
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Application of 38197-43-2, These common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, 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.

General procedure: To a mixture of 1-bromo-2-methoxynaphthalene (2.3mmol) and magnesium turnings (9.0mmol) in diethyl ether (10mL) was stirred at room temperature under argon atmosphere until white slurry was formed. To the resulting mixture was added benzene (10mL) to dissolve the material, and the mixture was stirred for 2h at room temperature under argon atmosphere. The solution of resulting Grignard reagent was added dropwise to a solution of 2-methoxy-1,3-dinitrobenzene (1.5mmol) in benzene (15mL), and the mixture was stirred for 8h at 50C. The reaction mixture was quenched with water and extracted with ethyl acetate (3¡Á15mL). The combined extracts were dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane as eluent) to give a precursor of the starting material, which was the corresponding dinitro compound (1.1mmol, 73% yield). A mixture of the corresponding dinitro compound (1.0mmol) and Pd/C (80mg; 10wt%) in ethanol (10mL) was stirred for 12h at room temperature under hydrogen atmosphere (H2 balloon). The reaction mixture was filtered over Celite and concentrated to give a diamino compound. To a solution of the resulting diamino compound and pyridine (30mmol) in dichloromethane (20mL) was added dropwise a solution of benzenesulfonyl chloride (3.0mmol) in dichloromethane (10mL), and the reaction mixture was stirred for 24h at room temperature. The mixture was concentrated, and the residue was purified by column chromatography on silica gel (dichloromethane/ethyl acetate/hexane as eluent) to give starting material 8a (0.98mmol, 98% yield). Compounds 8b and 8c were synthesized by the same procedure.

The synthetic route of 38197-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirakawa, Seiji; Wu, Xiangfei; Liu, Shiyao; Maruoka, Keiji; Tetrahedron; vol. 72; 34; (2016); p. 5163 – 5171;,
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Adding a certain compound to certain chemical reactions, such as: 6876-00-2, name is 1-Bromo-3-phenoxybenzene, 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 6876-00-2, HPLC of Formula: C12H9BrO

STEP A 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone A few drops of m-phenoxy-bromobenzene were added to a mixture of 16.6 g of magnesium (50% turnings) in 53 ml of tetrahydrofuran and the mixture was heated to 40-45 C. Crystallization began and the rest of 62.2 g of m-phenoxy-bromobenzene was added dropwise at reflux over 45 minutes. 183 ml of tetrahydrofuran were added and the mixture was refluxed for one hour and was cooled to 0 C. to obtain a solution of a magnesium compound. The said solution was then added at 0 C. over 40 minutes to a mixture of 40.8 g of sodium trifluoroacetate in 240 ml of tetrahydrofuran and the mixture was stirred for two hours and was poured into aqueous 0.1N hydrochloric acid solution. The mixture was extracted with ether and the ether phase was washed with water, with aqueous N sodium hydroxide and with water. The ether phase was added to two liters of methylene chloride and the mixture was evaporated to dryness under reduced pressure to obtain 56.2 g of raw 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone which was used as is for the next step.

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

Reference:
Patent; Roussel Uclaf; US4833163; (1989); 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H9BrO2

To magnesium (290 g, 12 mmol), 1-bromo-3,5-dimethoxybenzene(0.86 g 4.0 mmol) in THF (20 mL) was added dropwise under nitrogen atmosphere. The mixture was refluxed until magnesium was consumed and cooled to 0C subsequently. To the solution allylbromide (1.2 mL, 15 mmol) was added dropwise. After stirring for 2 h at room temperature the mixture was quenched with sat. NH4Cl aq. was added and extracted with ether and the subsequent purification by flash column chromatography (hexane-ethyl acetate=19 : 1) afforded 1-allyl-3,5-dimethoxybenzene (356 mg, 50%). The mixture of CS2 (35 mL), Al (0.40 g 74 mmol) and I2 (3 g 118 mmol) was refluxed for 2 hs and cooled down to room temperature. To the stirred solution, a solution of 1-allyl-3,5-dimethoxybenzene (0.75 g, 4.2 mmol) in CS2 (35 mL) was added dropwise. The reaction mixture was stirred under reflux for 12 h. The reaction mixture was quenched with water and extracted with Et2O. The combined organic phase washed with 1 M Na2S2O3 aqueous solution and dried over Na2SO4. The solvent was removed and the resulting residue was dissolved in THF, subsequent purification by flash column chromatography (CHCl3-methanol=5 : 1) afforded 2-allylhydroquinone (34 mg, 6%).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishiwaki, Keiji; Ohigashi, Kanae; Deguchi, Takahiro; Murata, Kazuya; Nakamura, Shinya; Matsuda, Hideaki; Nakanishi, Isao; Chemical and Pharmaceutical Bulletin; vol. 66; 7; (2018); p. 741 – 747;,
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Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of the ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt

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

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
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