Category: 63057-72-7

63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1-(Benzyloxy)-4-bromo-2-methoxybenzene

General procedure: n-BuLi (10.7 mmol, 1.6 M solution in hexanes) was slowly added at -78 C under N2 atm to a stirred solution of 1a (10.2 mmol) in THF (25 mL) then stirred for 30 min at the same temperature. Aldehyde 2a (11.3 mmol) in THF (25 mL) was added dropwise over a period of 5 min then the reaction mixture was stirred for 30 min at -78 C. The reaction mixture was allowed to warm to 0 C, quenched with saturated NH4Cl solution, and extracted into ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and the solvents were evaporated. The crude compound was purified by column chromatography (35% EtOAc/hexane) to get alcohol 3a as off-white solid (yield 55%).

The synthetic route of 63057-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pericherla, Kasiviswanadharaju; Shirazi, Amir Nasrolahi; Kameshwara Rao; Tiwari, Rakesh K.; Dasilva, Nicholas; McCaffrey, Kellen T.; Beni, Yousef A.; Gonzalez-Sarrias, Antonio; Seeram, Navindra P.; Parang, Keykavous; Kumar, Anil; Bioorganic and Medicinal Chemistry Letters; vol. 23; 19; (2013); p. 5329 – 5331;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 63057-72-7, The chemical industry reduces the impact on the environment during synthesis 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

At room temperature, 1-Benzyloxy-4-bromo-2-methoxybenzene 10 (1.70 mmol, 0.50 g) was dissolved in freshly distilled THF (7 mL) in an oven-dried three-neck flask under argon. The temperature was cooled down to -78 oC and n-BuLi (1.6M in hexane, 1.96 mmol, 1.22 mL) was added dropwise. The reaction mixture was stirred for 1 h at this temperature and a solution of 4-benzyloxy-3-methoxybenzaldehyde 9 (1.70 mmol, 0.412 g) in THF (4mL) was added dropwise. The reaction mixture was stirred at -78 oC for 1.5 h, allowed to warm at room temperature and stirred for another 2 h. Water (24 mL) was slowly added to the mixture which was then extracted three times with EtOAc. The organic layers were dried with MgSO4 and concentrated in vacuo. The crude product was dissolved in a minimum of EtOAc and 100 mL of hexanes were added to precipitate the desired product. After 12 h at 0 oC, the precipitate was filtered, lightly washed with cold EtOAc and dried in vacuo, yielding 0.618 g (79 %) of 11 as a white solid. mp = 94-100oC. 1H-NMR (500 MHz, CDCl3): deltaH7.46-7.29 (10H,m), 6.96-6.79 (6H,m), 5.72 (1H, s), 5.13 (4H, s), 3.86 (6H, s). 13C-NMR (125 MHz, CDCl3): deltaC 149.7, 149.5, 147.6, 137.2, 135.4, 128.6, 127.9, 127.3, 119.7, 119.7, 118.9, 113.7, 113.5, 111.0, 110.3, 75.7, 71.0, 56.0. IR (ZnSe): numax 1511, 1251, 1226, 1132, 1019, 1006, 754, 741, 696 cm-1. HRMS (ESI-TOF,m/z): calcd for C29H27O4 (M-H2O+H)+= 439.1904, found 439.1923. This compound has been also previously reported.4

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(Benzyloxy)-4-bromo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cardinal, Sebastien; Azelmat, Jabrane; Grenier, Daniel; Voyer, Normand; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 440 – 444;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 63057-72-7,Some common heterocyclic compound, 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, molecular formula is C14H13BrO2, 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.

1 -(benzyloxy)-4-bromo-2- methoxybenzene (18.2 g, 62 mmol) was suspended in 162 mL methanol and 18 mL water. N- Iodosuccinimide (18. lg, 81 mmol) and trifluoroacetic acid (3.8 mL, 50 mmol) were added sequentially. The mixture was warmed to 35 C and stirred for 7 hours in the dark. Water (54 mL) was added dropwise over 15 minutes, then the mixture was allowed to cool slowly to room temperature while stirring overnight. The crystalline product was filtered, and rinsed with a 6:4 mixture of methanol: water (2 x 20 mL). The solids were dried in vacuo at 50 C to provide 1- (benzyloxy)-4-bromo-5-iodo-2-methoxybenzene. 1H NMR (400 MHz, Chloroform-d) delta 7.45 – 7.32 (m, 5H), 7.29 (s, 1H), 7.10 (s, 1H), 5.07 (s, 2H), 3.84 (s, 3H). MS (m/z) 419.8 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Benzyloxy)-4-bromo-2-methoxybenzene, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 63057-72-7

4-bromo-3-methoxyphenol 10 (19.8 mmol, 5.80 g) was dissolved infreshly distilled THF (200 mL) in an oven-dried three-neck flask underargon. Temperature was cooled down to -78 oC and the solution wasstirred for 30 minutes before dropwise addition of n-BuLi (1.6N in THF,21.8 mmol, 13.6 mL). Once the addition of n-BuLi was completed, themixture was stirred for another 30 minutes at -78 oC before the dropwise addition of freshlydistilled trimethyl borate (59.4 mmol, 6.75 mL) at this temperature. The reaction mixture wasallowed to warm at room temperature and stirred for 5 h. The temperature was cooled down to-20 oC and HCl 1N was slowly added to reach pH = 2-3. The reaction mixture was allowed towarm at room temperature and extracted three times with EtOAc. The organic layers werecombined, washed with brine, dried with MgSO4 and concentrated in vacuo until precipitationoccurred. An amount of hexanes was then added to maximize precipitation. The solution wasfiltered and the solid was filtered and dried under vacuum. The precipitation/filtration procedurewas repeated twice, yielding a total of 3.72 g (73%) of 4 as a white powder. mp = 184-189 oC.1H-NMR (500 MHz, CDCl3): delta = 4.02 (3H, s), 5.26 (2H, s), 7.01 (1H, d, J = 8.33), 7.31-7.50(5H, m), 7.77 (2H, dd, J = 7.78, 1.28). 13C-NMR (125 MHz, CDCl3): delta =56.05, 70.62, 112.97,117.98, 127.21, 127.96, 128.64, 129.71, 136.81, 149.06, 152.09. 11B-NMR (160 MHz, CDCl3): delta= 27.69. IR (NaCl): numax 1502, 1455, 1398, 1249, 1217, 1183, 1134, 1012, 846, 795, 746,697cm-1. HPLC (Retention time, %): 16.92 min, >99%. HRMS (ESI-TOF, m/z): calcd forC14H14BO3 (M-H2O+H)+ = 241.1033, found 241.1031.

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:
Article; Cardinal, Sebastien; Voyer, Normand; Tetrahedron Letters; vol. 54; 38; (2013); p. 5178 – 5180;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 63057-72-7, name is 1-(Benzyloxy)-4-bromo-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. Application In Synthesis of 1-(Benzyloxy)-4-bromo-2-methoxybenzene

A solution of 2 (4.0 g, 13.7 mmol) in dry THF (40 mL) at -78 C. was treated with n-BuLi (2.5 M, 6.0 mL, 15.0 mmol) for 15 min to produce 3. To this solution, 5 (3.1 g, 12.2 mmol) in dry THF (40 mL) was added slowly over a 10 min period. The reaction mixture turned light brown in color and stirring was continued for 1 h. The reaction was quenched by the addition of saturated aqueous NH4Cl (10 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (3×25 mL) and the combined organic layer was washed with brine (15 mL). Volatiles were evaporated under reduced pressure and the crude residue was purified by column chromatography using 20% acetone/hexane as the eluent to afford the title compound 6 as a white solid (2.6 g, 46%).

The synthetic route of 1-(Benzyloxy)-4-bromo-2-methoxybenzene has been constantly updated, and we look forward to future research findings.