4-Bromopyridinium chloride → 4-(4-Pyridyl)benzaldehyde

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Reaction Steps

This aldehyde was prepared using the procedure for 4-pyridin-2-yl-benzaldehyde in Example 126 from 4-bromopyridine hydrochloride, triethylamine and 4-formylboronic acid to give a yellow crystalline solid (51%): mp=90-91° C.; Rf=0.08 (30% EtOAc/hexanes); IR (KBr) 1697, 1595, 1214, 1169, 801 cm−1; 1H NMR (CDCl3) δ 7.74 (d, 2H, J=5.8 Hz), 7.84 (d, 2H, J=8.3 Hz), 8.05 (d, 2H, J=8.1 Hz), 8.77-8.78 (m, 2H), 10.11 (s, 1H). LRMS 184 (M+H).

Provenance & Evidence