反应详情

温度

37.5 °C

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (3 ml), 4-methoxy-3-nitroaniline (504 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture at 35-40° C. At the end of the addition of the aniline, extra t-butylnitrite (180 μl, 1.5 mmol) was added to the reaction mixture which then was stirred at 40° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. The crude product was dissolved in ethyl acetate-heptane (1:2, 20 ml) and filtered through a pad of silica. The solvent was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 97:3) gave 230 mg (40%) allyl-4-methoxy-3-nitrobenzene as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.45, (d, 1H, J=2.7 Hz), 7.27, (d, 1H, J=8.6 Hz), 7.10, (dd, 1H, J=8.6, 2.7 Hz), 6.02-5.90, (m, 1H), 5.12-5.02, (m, 2H), 3.86, (s, 3H), 3.62, (m, 2H, J=6.4 Hz); 13C NMR (CDCl3, 100 MHz) δ 158.8, 150.0, 135.9, 133.2, 127.2, 120.2, 117.1, 109.6, 56.2, 36.8; Anal HRMS Calcd. for C10H11NO3 (M): 193.0739. Found: 193.0743

1. additionwas added to the reaction mixture which
2. customThe volatile material in the reaction mixture was removed at reduced pressure
3. dissolutionThe crude product was dissolved in ethyl acetate-heptane (1:2, 20 ml)
4. filtrationfiltered through a pad of silica
5. customThe solvent was removed at reduced pressure