Month: July 2021

Application of 701-07-5, 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. 701-07-5 name is 2-(2′-Bromophenoxy)propane, 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.

Step 2: magnesium (350 mg, 14.42 mmol) was suspended in small amount of dry THF. Few crystals of iodine was added followed by 1 -bromo-2- isopropoxybenzene (1 g, 4.65 mmol) dissolved in dry THF. The reaction mixture was stirred at rt. The completion of halogen exchange was monitored by TLC. 2-Methyl-N-[(1 E)-(5-methylfuran-2-yl)methylidene]propane-2- sulfinamide (3.03 g, 13.95 mmol) diluted in dry THF was added dropwise at rt. The solution was stirred at rt for 2h. Sat. NH4CI was used to quench the reaction. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under vacuo. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (4:1 ) as eluent.

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

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (2016); A1;,
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Reference of 22094-18-4, A common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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 114A 3,3-dimethoxy-1-(3-(trifluoromethoxy)phenyl)cyclobutanecarboxamide The mixture of 1,3-dibromo-2,2-dimethoxypropane (1310 mg, 5.00 mmol), sodium tert-butoxide (1057 mg, 11 mmol) and 2-(3-(trifluoromethoxy)phenyl)acetonitrile (1006 mg, 5 mmol) in DMSO (12 mL) was stirred at 25 C. for about 16 hours, then heated at about 125 C. for about 30 minutes. The solution was cooled to room temperature, diluted with water, and extracted with ether three times. The organic phase was washed with saturated NH4Cl. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude mixture was purified by silica gel chromatography (50% Hexanes/EtOAc to 100% EtOAc) to afford the product (450 mg, 28.2%). LC-MS: m/z (M+H) 288. 1H NMR (400 MHz, DMSO-d6): delta 7.44-7.48 (t, J=8 Hz, 1H), 7.41 (s, 1H), 7.34-7.36 (d, J=7.6 Hz, 1H), 7.30 (s, 1H), 7.22-7.24 (d, J=8 Hz, 1H), 6.95 (s, 1H), 3.05 (s, 3H), 3.00 (s, 3H), 3.00-2.95 (d, J=14 Hz, 2H), 2.43-2.40 (d, J=12.8 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; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); 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. 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

1-fluoro-3-(trifluoromethoxy)benzene (7.5 g, 41.6 mmol) was dissolved in concentrated sulfuric acid (30 mL),and the mixuture was cooled to 0 C. KNO3 (1.04 g, 10.25 mmol) was added slowly in batches. The internal temperatureis keeped below 5 C. Upon completion of the addition, the mixture was stirred for 2 hours. An eice-water mixture (about50 mL) was added. The reaction solution was extracted with methyl tert-butyl ether (2033 mL), and the organic phaseswere combined, dried and filtered. The filtrate was concentrated and purified by flash silica gel column chromatographyto obtain 4-fluoro-1-nitro-2-(trifluoromethoxy)benzene (4.0 g, 42%).

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 1077-01-6.

Reference:
Patent; Shanghai Hansoh Biomedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; WEI, Mingsong; SUN, Guangjun; TAN, Songliang; GAO, Peng; WANG, Shaobao; XIU, Wenhua; ZHANG, Fujun; BAO, Rudi; (183 pag.)EP3205650; (2017); 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

Cyclohexanone (19.62 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-Cyclohexyl-3-fluoro-4-methoxyaniline (2.8 g, 63percent yield). MS m/z=224 [M+H].

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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Synthetic Route of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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Synthetic Route of 51388-20-6, These common heterocyclic compound, 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, 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.

A solution of 4-benzyloxyaniline hydrochloride (compound Ia, 12 g) in MeOH (200 mL) was treated with aqueous NaOH (2.04 g in 80 mL deionized water) and the resulting clear solution was concentrated to dryness to provide a residue of crude aniline free base.

The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
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Some common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, molecular formula is C9H13NO, 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. category: ethers-buliding-blocks

General procedure: 2-Hydroxynaphthalene-1-carboxylic acid or 1-hydroxynaphthalene-2-carboxylic acid (5.30 mmol) and appropriate alkoxyaniline (5.30 mmol) were suspended in 30 mL of dry chlorobenzene. Phosphorous trichloride (2.65 mmol) was added dropwise, and reacting mixture was heated in the microwave reactor for 15 min at 130 C using infrared flask-surface control of temperature. Solvent was evaporated in vacuum; residue solid was washed with 2M HCl and crystallized from aqueous ethanol. If necessary, column chromatography was used for further purification (mobile phase DCM:MeOH 19:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41406-00-2, its application will become more common.

Reference:
Article; Gonec, Tomas; Pospisilova, Sarka; Kauerova, Tereza; Kos, Jiri; Dohanosova, Jana; Oravec, Michal; Kollar, Peter; Coffey, Aidan; Liptaj, Tibor; Cizek, Alois; Jampilek, Josef; Molecules; vol. 21; 8; (2016);,
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Adding a certain compound to certain chemical reactions, such as: 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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 53087-13-1, SDS of cas: 53087-13-1

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (1.29 g, 52.8 mmcl) in dry THF (50 mL). The mixture was refluxed and about 5% of a solution of 3- bromophenol (13.9 g, 52.8 mmcl) was added. When the reaction had started, the solution of thebromide 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 mmcl) 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 (Na2SO4), filtered andconcentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

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

Reference:
Patent; MEDIVIR AB; KALAYANOV, Genadiy; PINHO, Pedro; WESTERLIND, Hans; WIKTELIUS, Daniel; WAeHLING, Horst; WO2015/56213; (2015); 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. 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, A new synthetic method of this compound is introduced below., SDS of cas: 29578-83-4

3-Bromo-5-methoxybenzoic acid To a vigorously stirred mixture of 1-Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMnO4 (3.14 g, 19.89 mmol) at 105 C. The mixture which turned to a black suspension was stirred 24 hours at 105 C., then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCl. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24% yield) as a white solid. MS: 229.1 [M+H]+, Rt(1)=1.18 min.

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; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
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Related Products of 171290-52-1, A common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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