Aniline → 2-Allyl-5-nitrobenzophenone

関与物質

反応条件

反応手順

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (3 ml), 2-amino-5-nitrobenzophenone (727 mg, 3.0 mmol) was added during 20 minutes while maintaining the temperature of the reaction mixture at 28-32° C. At the end of the addition of the aniline, extra t-butylnitrite (360 μl, 3 mmol) was added to the reaction mixture which then was stirred at 25° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 370 mg (46%) of 2-allyl-5-nitrobenzophenone as a light yellow oil. 1H NMR (CDCl3, 300 MHz) δ 8.29, (dd, 1H, J=8.6, 2.5 Hz), 8.18, (d, 1H, J=2.4 Hz), 7.81-7.74, (m, 2H), 7.69-7.60, (m, 1H), 7.57-7.45, (m, 3H), 5.93-5.88, (m, 1H), 5.09-5.95, (m, 2H), 3.53, (m, 2H, J=6.6 Hz).

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