1,3-Dibromopropane → HCID 61975301, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

N-methyl-3-methoxyaniline (1.0 g, 7.294 mmol) was dissolved in anhydrous DMF (20 mL), to which 1,3-dibromopropane (1.48 mL, 14.589 mmol), K2CO3 (3.018 g, 21.884 mmol) and 18-crown-6 (0.24 g, 1.458 mmol) were added at room temperature, and reaction mixture stirred at 35° C. for 24 hours. The remaining procedure was followed as described for compound 14 to obtain compound 15. Yield: 0.760 g (75%). 1H NMR (500 MHz, CDCl3): δ 2.16 (tt, 2H, J=6.5, 13.5 Hz, Hc), 2.98 (s, 3H, NCH3, Ha), 3.46-3.54 (m, 4H, Hb and Hd), 3.83 (s, 3H, OMe), 6.32-6.66 (m, 2H, Hg and Hi), 6.38-6.42 (m, 1H, Ha), 7.16-7.21 (m, 1H, Hf); 13C NMR (125 MHz, CDCl3): δ 29.90 (Cc), 31.34 (Cd), 38.65 (Ca), 50.79 (Cb), 55.02 (OCH3), 98.77 (Ci), 101.26 (Ce), 105.31 (Cg), 129.81 (Cf), 150.32 (Cj), 160.72 (Ch). EI-MS: [M+H]+ C11H7BrNO calcd 258.05, obsd 258.04.

Herkunft & Nachweise