Aniline → 1-Allyl-3-nitrobenzene

Temperatur

35 °C

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (30 ml), 3-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 47:3) gave 420 mg of 3-allylnitrobenzene as a light yellow oil containing 36% of 3-bromonitrobenzene. This corresponds to 50% yield of 3-allylnitrobenzene. 1H NMR (CDCl3, 400 MHz) δ 8.10-8.08, (m, 1H), 8.08-8.05, (m, 1H), 7.56-7.51, (m, 1H), 7.50-7.44, (m, 1H), 6.02-5.91, (m, 1H), 5.20-5.10, (m, 2H), 3.50, (d, 2H, J=6.7 Hz); 13C NMR (CDCl3, 100 MHz) δ 148.8, 142.5, 136.1, 135.3, 129.7, 123.9, 121.8, 117.8, 40.1.

1. additionwas added to the reaction mixture which
2. customThe volatile material in the reaction mixture was removed at reduced pressure

ORD-Eintrag

ord-d6604ea32a7a4a908cd788356d5a9f89

Quelldatensatz

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06284894B1