Related Products of 57946-63-1, These common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, 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.
Diethyl ethoxymethylenemalonate (2.3 g, 10.6 mmol, 2.5 eq.) was added to a solution of 2-bromo-4-(trifluoromethyl)aniline (25) (1.0 g, 4.2 mmol, 1.0 eq.) in toluene (6 mL). The resulting mixture was refluxed for 11 h. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue obtained was purified by column chromatography (SiO2, cyclohexane/ethyl acetate, 100/0 to 80/20, v/v) to afford the desired product 26 (1.5 g, 3.7 mmol, 88percent) as a white solid. Rf (SiO2, cyclohexane/ethyl acetate, 9/1, v/v): 0.34; Mp: 90-92 °C; IR (cm-1): 1682 (nuC=O), 1646 (nuC=C), 1596 (deltaN-H), 1321 (nuCF3), 1245 (nuas C-O-C), 1077 (nus C-O-C); 1H NMR (CDCl3, 400 MHz) delta 11.38 (d, 1H, 3JNH-Ha= 12.7 Hz, NH), 8.48 (d, 1H, 3JHa-NH = 12.7 Hz, Ha), 7.86 (d, 1H, 4JH3-H5= 1.4 Hz, H3), 7.61 (m, 1H, H5), 7.36 (d, 1H, 3JH6-H5= 8.5 Hz, H6), 4.36 (q, 2H, 3JHd-He or Hd?-He?= 7.1 Hz, Hd or Hd?), 4.28 (q, 2H, 3JHd-He or Hd?-He?= 7.1 Hz, Hd or Hd?), 1.39 (t, 3H, 3JHe-Hd or He?-Hd?= 7.1 Hz, He or He?), 1.34 (t, 3H, 3JHe-Hd or He?-Hd?= 7.1 Hz, He or He?); 13C NMR (DMSO-d6, 125 MHz) delta 167.9 (Cc or Cc?), 164.8 (Cc or Cc?), 150.0 (Ca), 140.9 (C1), 130.5 (d, 3JC3-F = 4 Hz, C3), 126.6 (d, 3JC5-F = 4 Hz, C5), 125.6 (q, 2JC4-F = 33 Hz, C4), 123.7 (d, 1JCF3-F = 270 Hz, CF3), 117.2 (C2), 112.9 (C6), 97.5 (Cb), 60.7 (Cd or Cd?), 60.4 (Cd or Cd?), 14.6 (Ce or Ce?), 14.5 (Ce or Ce?); HRMS calculated for C15H1579BrF3NO4 [M+H]+ m/z 410.0215, found C15H1579BrF3NO4 [M+H]+ m/z 410.0189 (100percent); C15H1581BrF3NO4 [M+H]+ m/z 412.0157 (98percent).
The synthetic route of 57946-63-1 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Liu, Jianrong; Maisonial-Besset, Aurelie; Wenzel, Barbara; Canitrot, Damien; Baufond, Ariane; Chezal, Jean-Michel; Brust, Peter; Moreau, Emmanuel; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 548 – 560;,
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