Tag: M.W=200-300

Electric Literature of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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.

(0677) 4-Bromo-2-methoxyaniline (6.8 g, 33.7 mmol) and di-tert-butyl dicarbonate (8.9 g, 40.8 mmol) were dissolved in tetrahydrofuran (100 mL). Under the protection of nitrogen gas, the reaction was carried out under reflux for 22 h, and the mixture was cooled. The solvent was removed by distillation under reduced pressure, and ethyl acetate (150 mL) was added. The mixture was washed with 1 mol/L hydrochloric acid, and the water phase and the organic phase were separated. The organic phase was dried with anhydrous sodium sulfate, and filtrated under suction. The filtrate was concentrated to get the title compound (8.3 g, yield: 81.6%).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

b. 4-(5-Bromo-2-methoxyanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 5-bromo-2-methoxyaniline (39 mg, 0.193 mmol) similar to Example 117 and isolated as a tan solid (26 mg, 32%). 1H NMR (CDCl3): 9.67-9.66 (m, 1H), 8.77-8.71 (m, 3H), 7.55 (s, 1H), 7.48-7.43 (m, 1H), 7.24 (dd, J=2.4, 8.7 Hz, 1H), 6.92 (s, 1H), 6.83 (d, J=9.0 Hz, 1H), 3.93 (s, 3H).

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; Cytovia, Inc.; US2003/69239; (2003); A1;,
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Related Products of 29578-83-4, 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. 29578-83-4 name is 1-Bromo-3-methoxy-5-methylbenzene, 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.

A mixture of D-6-1 (100 g, 497 mmol), NBS (88.5 g, 497 mmol), and AIBN (10 g, 50 mmol) in CCl4 (700 mL) is heated to reflux for 12 h. The mixture is cooled to ambient temperature, diluted with H2O, and extracted with EtOAc. The organic layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to afford D-6-2 (48 g, 42% yield).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27060-75-9

General procedure: An argon flushed pressure tube was charged with indole (59 mg, 0.5mmol), bromobenzene (62 muL, 0.5 mmol), Mo(CO)6 (132 mg, 0.5mmol), DBU (75 muL, 0.5 mmol), K3PO4 (106 mg, 0.5 mmol), Pd(OAc)2(3.4 mg, 3 mol%), BuPAd2 (10.8 mg, 6 mol%), and DMF (3 mL). The tubewas subsequently sealed and the mixture was stirred at 120 C for 16h. Afterwards, the reaction mixture was diluted with CH2Cl2 (3 × 5mL) and washed with H2O (3 × 5 mL). The aqueous layer was extractedwith CH2Cl2 (2 × 5 mL), the combined organic phases were dried(Na2SO4), and the solvent was evaporated. The crude product was purifiedby column chromatography (pentane-EtOAc (8:2) with additionof 0.5% Et3N) to give benzoylindole as a viscous oil that solidifiedon standing; yield: 98 mg (89%); mp 64-65 C.

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 27060-75-9.

Reference:
Article; Wu, Xiao-Feng; Oschatz, Stefan; Sharif, Muhammad; Langer, Peter; Synthesis; vol. 47; 17; (2015); p. 2641 – 2646;,
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Synthetic Route of 458-50-4,Some common heterocyclic compound, 458-50-4, name is 4-Bromo-3-fluoroanisole, 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.

A degassed solution of 3-amino-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester (206 g, 1.0 mmol), l-bromo-2-fluoro-4-methoxy-benzene (246 mg, 1.2 mmol), Pd2dba3 (46 mg, 0.050 mmol), Xantphos (58 mg, 0.10 mmol) and K3PO4 (254 mg, 1.2 mmol) in toluene (5 ml) was heated to 1100C then stirred for 18 hours. The reaction mixture was cooled to ambient temperature then diluted with EtOAc and filtered through a pad of celite. The filtrate was concentrated in vacuo to give a black oil. The oil was purified by flash chromatography (Si-SPE, MeOH: DCM, gradient 0: 100 to 10:90) to provide the title compound as a yellow oil (130 mg, 39percent). LCMS (method B): Rx = 2.93 min, M+H+ = 331.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-fluoroanisole, its application will become more common.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
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Electric Literature of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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.

To a solution of 4-bromo-2-methoxyaniline (4.0 g, 20 mmol) in concentrated hydrochloric acid (40 mL) was added dropwise sodium nitrite (1.4 g, 21 mmol) and water (2 mL) solution while maintaining at -20C, and the mixture was stirred at the same temperature for 15 min. The mixture was warmed to 0C, and the mixture was stirred at the same temperature for 20 min, and further, a solution of tin chloride·2 hydrate (17 g, 74 mmol) in concentrated hydrochloric acid (140 mL) was added dropwise to the reaction mixture while maintaining at -20C. After stirring at the same temperature for 10 min, and the mixture was stirred at room temperature for 40 min. The precipitate was collected by filtration, and washed with ice water and diethyl ether. To the filtered material was added ethyl acetate and 10% aqueous potassium carbonate, and the insoluble material was filtered off. The aqueous layer of the filtrate was extracted with ethyl acetate, the organic layer was combined, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a pale yellow solid (3.4 g, 78%). 1H NMR (CDCl3) delta: 3.49 (2 H, br), 3. 84 (3 H, s), 5.61 (1 H, br), 6.85 – 6.88(2 H, m), 7.06 (1 H, dd, J=2.1, 8.7 Hz).

Statistics shows that 4-Bromo-2-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 59557-91-4.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2455380; (2012); A1;,
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These common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-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. Product Details of 103291-07-2

PREPARATION 12 3-(4-Fluoro-3-methoxyphenyl)pyridine A solution of 15.6 g (76.1 mmole) of 1-bromo-4-fluoro-3-methoxybenzene in 67 ml of tetrahydrofuran was added dropwise, with stirring, under nitrogen, to 1.92 g (79.1 mmole) of dried magnesium turnings. Stirring was continued for 1 hour and then the supernatant liquid was removed to give a solution of 4-fluoro-3-methoxyphenylmagnesium bromide. In a separate flask, 7.3 ml (76.1 mmole) of 3-bromopyridine was dissolved in 23 ml of tetrahydrofuran and 880 mg (0.76 mmole) of tetrakis-triphenylphosphine palladium was added. This latter mixture was heated to reflux, and the above Grignard solution was added dropwise, during 10 minutes, with stirring. The resulting mixture was refluxed for 1 hour and then it was stirred overnight at room temperature. The reaction mixture was diluted with 100 ml of water, followed by 100 ml of 10% hydrochloric acid, and the resulting solution was washed with dichloromethane. The aqueous phase was basified with sodium bicarbonate and then it was extracted with dichloromethane. The combined extracts were dried using potassium carbonate and evaporated in vacuo to give 12.3 g (79%) of the title compound as a reddish oil.

The synthetic route of 4-Bromo-1-fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4593037; (1986); A;,
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These common heterocyclic compound, 143-24-8, name is 2,5,8,11,14-Pentaoxapentadecane, 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 2,5,8,11,14-Pentaoxapentadecane

Comparative Example 1 was conducted in the same manner as in Example 1 except that 4 mmole of 3-hydroxypyridine was used as promoter instead of imidazole and except the reaction conditions. 1 mmole of Co2(CO)8 was used and 200 mmole of ethylene oxide was used. The reaction conditions of Comparative Example 1 were shown in Table 2.

The synthetic route of 2,5,8,11,14-Pentaoxapentadecane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co. Ltd.; US6348632; (2002); B1;,
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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. Recommanded Product: 1516-96-7

A -78 C. solution of 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (2.142 g; 7.158 mmol) in dry THF (15 mL) was treated with n-butyllithium (7.00 mL, 1.13M in hex, 7.88 mmol). The solution was stirred at -78 C. for 15 min, then treated with trimethylborate (976 muL; 8.59 mmol). The reaction was allowed to warm to ambient temperature and evaporated to a thick oil.

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; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., name: ((3-Bromopropoxy)methyl)benzene

Compound 3F: 1 -[3-(Benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazoleA mixture of 4-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1 /-/-pyrazole (5.0 g, 26 mmol), potassium carbonate (4.27 g, 30.9 mmol) and 1-bromo-3-benzyloxypropane (6.20 g, 27.0 mmol) in DMF (20 mL) was stirred at 80 °C overnight, quenched with water (20 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (2 x 30 mL), brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ISCO system: EtOAc/Heptane = 30- 70percent) to afford 7.67 g of the title compound as a light-yellow oil (87percent). 1H NMR (CDCI3, 400 MHz): delta = 7.80 (s, 1 H), 7.66 (s, 1 H), 7.30-7.36 (m, 5H), 4.48 (s, 2H), 4.28 (t, J = 6.8 Hz, 2H), 3.43 (t, J = 5.8 Hz, 2H), 2.17 (m, 2H), 1.33 (s, 12H). MS (ES+): m/z = 343.36 [MH+]. HPLC: iR = 4.20 min ( ZQ3: polar_5 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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
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