These common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. Product Details of 327-52-6
To a dryflask (equipped with a magnetic stirrer and a rubber septum) filledwith argon, 1-bromo-2,4,5-trifluorobenzene 45 (4.39 mL, 37.5 mol)and anhydrous THF (10.6 mL) were added and cooled to 20 C;2 M solution of iPrMgCl in THF (22.5 mL) was slowly added tothe reaction mixture, the reaction temperature was adjusted to10 C and the mixture was stirred for one hour until theGrignard exchange reaction was completed. The resulting solutionof 46 was added dropwise to the solution of ethyl 4-iodobenzoate38 (0.50 mL, 3.0 mmol), tetrakis(triphenylphosphine)palladium(299 mg, 0.15 mmol) and HMTA (21 mg, 0.15 mmol) in anhydrousTHF (20 mL) at 0 C. The reaction mixture was maintained at 0 Cfor one hour and then stirred overnight at room temperature.The solvent was removed by evaporation and the residue was purifiedby column chromatography using diethylether/hexane (1:10)as an eluent to obtain 0.70 g (83%) of compound 47 as white crystals.Mp 73-75 C; 1H NMR (400 MHz, CDCl3): d (ppm) 1.42 (t,J = 7.2 Hz, 3H, CH3), 4.41 (q, J = 7.2 Hz, 2H, CH2), 7.02-7.08 (m,1H, Ar-H), 7.25-7.32 (m, 1H, Ar-H), 7.56 (d, J = 8.8 Hz, 2H, Ar-H),8.12 (d, J = 8.8 Hz, 2H, Ar-H); 13C NMR (100 MHz, DMSO-d6): d(ppm) 14.08, 60.88, 106.80 (dd, 1H, 2JC,F = 21.2 Hz, 2JC,F0 = 29.7 Hz),118.51 (dd, 1H, 3JC,F = 4.2 Hz, 2JC,F = 19.9 Hz), 124.00 (ddd,3JC,F = 4.5 Hz, 3JC,F = 5.7 Hz, 2JC,F = 15.7 Hz), 129.14 (d, 1H, 3JC,F =3.2 Hz), 129.35, 129.54, 137.71, 146.53 (ddd, 4JC,F = 3.3 Hz,2JC,F = 13.6 Hz, 1JC,F = 241,4 Hz), 149.08 (dt, 3JC,F = 13.2 Hz, 2JC,F =13.6 Hz, 1JC,F = 248.5 Hz), 154.39 (ddd, 4JC,F = 1.2 Hz, 3JC,F = 9.8 Hz,1JC,F = 245,1 Hz), 165.28; HR-MS (ESI): m/z calcd for C15H12O2F3 [M+H]+ 281.0789, found: 281.0787; HPLC tR = 13.669 min (97.2%,method 2).
The synthetic route of 1-Bromo-2,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.
Reference:
Article; Berne, Sabina; Kova?i?, Lidija; Sova, Matej; Kra?evec, Nada; Gobec, Stanislav; Kri?aj, Igor; Komel, Radovan; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4264 – 4276;,
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