Synthetic Route of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.
Step 1: Methyl 2-(3-(benzyloxy)phenyl)-2-hydroxy-2-phenylacetate Magnesium turnings (40.9 g, 1.71 mol) were placed in the three necked round bottom flask under argon. Anhydrous THF (1800 mL) and crystals of iodine (6.18 g, 0.024 mol) were added then 1-(benzyloxy)-3-bromobenzene (384.69 g, 1.46 mol) was added in portions. The internal temperature rose to 60 C. and the reaction foamed. The reaction was stirred for 2.5 hours at reflux. In another flask, a solution of methyl benzylformate (200.00 g, 1.22 mol) in anhydrous THF (2000 mL) was cooled to -70 C. under argon and to this the Grignard reagent was added dropwise over 3 hours. The reaction was allowed to slowly warm to room temperature and stirred at this temperature for 18 hours. The reaction was quenched with ammonium chloride solution. Layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic fractions were washed with brine and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to afford an oil. The resultant oil was evaporated with hexane twice to afford a solid (473.15 g). The solid was refluxed with 4730 ml hexane (10 ml/g) for 5 min, then allowed to cool to room temperature and stirred for 1 hour, then filtered and washed with hexane to obtain 386.34 g (HPLC: 83.85%). The product was crystallized in 3930 ml iPrOH (13 ml/g). The mixture was milky at reflux, was filtered (solid: 5.85 g, HPLC: 95.95%) and the filtrate was allowed to crystallized for 18 hours. The resulting precipitate was stirred for 1.5 hour at 10 C., then filtered and washed with hexane to afford the title product (180.54 g, 42%). 1H NMR (400 MHz, DMSO-d6); delta 7.44-7.22 (m, 11H), 6.98-6.93 (m, 2H), 6.92-6.88 (m, 1H), 6.68 (s, 1H, OH), 5.05 (s, 2H), 3.70 (s, 3H).
The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); A1;,
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