Water → 6-(5-Bromo-furan-2-yl)-nicotinonitrile

Participants

Reaction Steps

Continuing with Scheme 1, to a solution of 1 (5.1 g, 30 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (5.87 g, 33 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold-water. The precipitate that formed was collected, washed with water and dried to give the analytically pure product 2 in 90.4% yield, mp 196° C. 1H nmr (DMSO-d6); δ 6.86 (d, J=3.6 Hz, 1H), 7.38 (d, J=3.6 Hz, 1H), 7.86 (d, J=8.1 Hz, 1H), 8.33 (dd, J=8.1, 2.1 Hz, 1H). 8.98 (d, J=2.1 Hz, 1H). 13C nmr; δ 153.4, 152.7, 149.6, 140.9, 125.4, 117.9, 117.0, 115.0, 114.9, 106.9. MS (m/z, rel.int.); 248 (M+, 100), 220 (10), 169 (25), 141 (80), 114 (30). Calcd for C10H5BrN2O: C, 48.22; H, 2.02; N, 11.25. Found. C, 48.47; H, 2.01; N, 11.34.

Provenance & Evidence