Aniline → p-Allylnitrobenzene

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To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (30 ml), 4-nitroaniline (414 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture at 34-36° 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 35° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 330 mg of 4-allylnitrobenzene as a light yellow oil containing 15% of 4-bromonitrobenzene. This corresponds to 55% yield of 4-allylnitrobenzene. 1H NMR (CDCl3, 300 MHz) δ 8.16, (m, 2H, J=8.6 Hz), 7.35, (m, 2H, J 8.6 Hz), 6.02-5.88, (m, 1H), 5.19-5.08, (m, 2H), 3.49, (d, 2H, J=6.6 Hz).

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