Bromide ion → 2-Cyanobenzyltriphenylphosphonium bromide

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Bromination of o-tolunitrile with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine (1.2 equiv.), using the procedure described in example 102, except that the reaction time for the bromination was 2 h, gave the phosphonium salt (547) (70%) as a light brown powder, mp (CH2Cl2/benzene) 237–241° C. 1H NMR (CDCl3) δ 7.90 (dd, J=7.8, 2.3 Hz, 1H), 7.85–7.63 (m, 15H), 7.52 (br t, J=7.7 Hz, 1H), 7.44 (br d, J=7.5 Hz, 1H), 7.38 (tdd, J=7.6, 2.1, 1.0 Hz, 1H), 5.86 (d, J=14.7 Hz, 2H). Found: C, 67.88; H, 4.42; N, 3.09. C26H21BrNP requires C, 68.13; H, 4.62; N, 3.06.

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