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;,
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