Category: 5467-58-3

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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, A new synthetic method of this compound is introduced below., SDS of cas: 5467-58-3

5-a. Synthesis of 1-methoxy-4-{3,5-(diphenyl)phenyl}naphthalene 1-Methoxy-4-{3,5-(diphenyl)phenyl}naphthalene was synthesized as follows. 1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 3,5-diphenylphenylboronic acid 37.6 g (0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (500 mL) and water (600 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (1000 mL) and filtered. The filtrate was concentrated and recrystallized in methanol (800 mL). The resulting solid was filtered and washed with hexane (300 mL) to obtain a product (23.5 g, 0.061 mol, 57.6%).

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; SFC CO., LTD.; US2011/108827; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-methoxynaphthalene

2-(4-Methoxy-1-naphthyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (S2). 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.92 mL, 15.00 mmol) was added dropwise to a solution of 1-bromo-4-methoxynaphthalene S1 (1.19 g, 5.00 mmol), NEt3 (2.79 mL, 20 mmol) and Pd(ddpf)Cl2.CH2Cl2 (510 mg, 0.625 mmol) in anhydrous dioxane (15 mL) and the reaction mixture heated at 100 C. for 23 h. After cooling to room temperature, the reaction was quenched cautiously with water (20 mL) and extracted with CH2Cl2 (3¡Á35 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2; EtOAc/heptane; 0-30%) afforded the pinacol ester as an off-white solid (1.09 g, 77%). 1H NMR (400 MHz, CDCl3) delta=1.41 (s, 12H), 4.02 (s, 3H), 6.82 (d, J=7.8 Hz, 1H), 7.43-7.48 (m, 1H), 7.53-7.57 (m, 1H), 8.04 (d, J=7.8 Hz, 1H), 8.28 (dd, J=0.9, 8.3 Hz, 1H), 8.75 (d, J=8.3 Hz, 1H). 13C NMR (100 MHz, CDCl3) delta=25.1, 55.6, 83.5, 103.3, 122.1, 125.0, 125.5, 127.0, 128.3, 137.0, 138.3, 158.3. HRMS (ESI+) (m/z): [M+H]+ calcd. for C17H22BO3, 285.1657; found, 285.1643.

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 5467-58-3.

Reference:
Patent; Hadjifrangiskou, Maria; Almqvist, Fredrik; Shaffer, Carrie L.; Good, James; (66 pag.)US2017/233409; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5467-58-3, 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 5467-58-3 as follows.

To a solution of 1-bromo-4-methoxynaphthalene (4.72 g, 20 mmoL) in 1, 4-dioxane /H2O (80 mL/20mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (5.32 g, 10 mmol), Pd (dppf) Cl2 (1462 mg, 2.0 mmol) and Cs2CO3 (9.75 g, 30 mmol) and the mixture was heated at 70 for 5 hours. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA=5: 1) to give product as an oil (4.1 g in 69% yield). [M+H] +=297.

According to the analysis of related databases, 5467-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem