Abstract
Reaction of anhydrous cuprous cyanide with aryl bromides produced aryl cyanides (Rosenmund–von Braun reaction) under microwave irradiation in a short time and in high yield.
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Selected spectroscopic data: product (3 ): 1H NMR (80 MHz, CDCl3), δ: 7.2–7.5 (q, 4H, Ar, AA'BB’; J AB=J A'B’=7.83 Hz), 2.42 (s, 3H, CH3); IR (neat), cm−1: 3060, 3040, 2963, 2926, 2223 (CN), 1561, 1502; product (4 ): 1H NMR (80 MHz, CDCl3), δ: 7.3 (d, 2H, Ar; J =6.92 Hz), 6.8 (d, 2H, Ar; J =6.92 Hz), 3.7 (br, 2H, NH2); IR (KBr), cm−1: 3470, 3380, 3060, 3053, 2210 (CN), 1620, 1600; product (6 ): 1H NMR (80 MHz, CDCl3), δ: 7.5–8.2 (m, Ar); IR (neat), cm−1: 3090, 3057, 2223 (CN), 1620, 1513; product (7 ): 1H NMR (80 MHz, CDCl3), δ: 8.7 (dd, 1H, Ar; J 1=5.11 Hz, J 2=2.0 Hz), 7.5–7.8 (m, 3H, Ar), IR (neat), cm−1: 3060, 3003, 2239 (CN), 1590, 1460, 1430.
20.c.f : The Aldrich Library of FT-IR and NMR Spectra