Azobisisobutyronitrile → Di-tert-butyl [6-(bromomethyl)pyridin-3-yl]imidodicarbonate

Participants

Reaction Conditions

Reaction Steps

A mixture of di-tert-butyl (6-methylpyridin-3-yl)imidodicarbonate (Compound 260D, 15 g, 49 mmol), NBS (8.2 g, 49 mmol) and AIBN (1.0 g) in CCl4 (200 mL) was stirred at 100° C. overnight. TLC showed the reaction was complete. The reaction mixture was concentrated and residue was purified by column chromatography to afford the desired compound (5.0 g, yield: 26%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ=1.41 (s, 18 H), 4.53 (s, 2 H), 7.44 (dd, J=2.4, 8.0 Hz, 1 H), 7.67 (d, J=8.4 Hz, 1 H), 8.33 (dd, J=2.4, 8.0 Hz, 1 H).

Provenance & Evidence