24398-88-7, A common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, molecular formula is C9H9BrO2, 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.
1-(6-(dibutyl(3-(ethoxycarbonyl)phenyl)stannyl)hexyl)-3-ethyl-1H-imidazol-3-ium bromide I’a-14(Br-) A dried 50 mL Schlenk tube was flushed with argon and charged with zinc dust (1.36 g, 20.8 mmol, 5 eq) and cobalt(II) bromide (0.095 g, 0.4190.434 mmol, 0.1 eq). The mixture was activated under vacuum at 150C during 4 h. Acetonitrile (5 mL) was added to the cooled mixture then trifluoroacetic acid (0.15 mL) and 1,2-dibromoethane (0.1 mL) were added and the resulting solution stirred for additional 15 minutes (an increase of temperature was observed). Then ethyl 3-bromobenzoate (1.46 g, 6.36 mmol, 6.3 eq) was introduced to the mixture which was stirred at room temperature for 12 h. The resulting solution of arylzinc reagent was introduced dropwise to the ionic liquid (Va-1) (529 mg, 1.0 mmol, 1 eq) in solution in THF (6 mL). After 18 h of stirring at room temperature, the resulting mixture was filtered through a short pad of silica gel then extracted with CH2Cl2 (3 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (CH2Cl2 to CH2Cl2/MeOH 90:10) to afford compound I’a-14(Br-) as viscous yellow oil (450 mg, 70 %). 1H NMR (CDCl3): delta 10.17 (s, 1H), 8.14 (bs, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.39 (dd, J = 7.5 Hz, J = 7.5 Hz, 1H), 7.30 (bs, 1H), 7.23 (bs, 1H), 4.48-4.33 (m, 4H), 4.32 (t, 2H, J = 7.2 Hz), 1.89-1.78 (m, 2H), 1.61-1.47 (m, 9H), 1.42-1.24 (m, 11H), 1.13-1.00 (m, 6H), 0.87 (t, J = 7.2 Hz, 6H). 13C NMR 75 MHz (CDCl3) delta (ppm): 166.8, 141.9, 140.6, 136.9, 135.9, 129.4, 128.8, 127.5, 122.0, 121.8, 60.6, 49.8, 45.1, 33.4, 30.0, 28.7, 27.0, 26.3, 25.5, 15.5, 14.4, 13.4, 9.4, 9.3. HRMS (FAB) calcd. for C28H47N2O2Sn 563.2654 [M-Br]+; found 563.2675.
The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Centre National de la Recherche Scientifique (CNRS); UNIVERSITE DE NANTES; UNIVERSITE D’ANGERS; Universite du Maine; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre Hospitalier Universitaire De Nantes; Legoupy, Stephanie; Faye, Djibril; Gestin, Jean-Francois; Rajerison, Holisoa; Faivre-Chauvet, Alain; Boeda, Fabien; EP2891657; (2015); A1;,
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