N-bromobutanimide → 3-(Bromomethyl)pyridine-2-carbonitrile

Participants

Reaction Steps

Synthesized from 3-methylpicolinonitrile (1.00 g, 8.47 mmol), NBS (1.66 g, 9.31 mmol) and DBPO (103 mg, 0.42 mmol) in CCl4 according to Method A. Yield: 616 mg, 3.12 mmol, 37%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 4.63 (s, 2H), 7.54 (dd, J=7.9, 4.9 Hz, 1H), 7.92 (dd, J=7.9, 1.5 Hz, 1H), 8.64 (dd, J=4.9, 1.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=26.8, 115.2, 127.1, 133.2, 138.1, 138.3, 150.5; MS (ESI): m/z=199.79 [M+H]+.

Provenance & Evidence