4-Bromo-2-nitroaniline → Benzenamine, 2-nitro-4-(2-propenyl)-

Participants

Reaction Steps

Prepared from 4-bromo-2-nitroaniline 17 (1.70 g, 7.84 mmol) and allyltributyltin (3.38 g, 10.2 mmol) as a yellow solid in 96% yield as described above for 5: mp 29°-31° C.; IR (KBr) 3490, 3374, 1638, 1518, 1341, 1253; 1H NMR δ7.90 (1H, d, J=2.0), 7.19 (1H, dd, J=8.5, 2.0), 6.77 (1H, d, J=8,5), 6.05 (NH, brs), 6.00-5.80 (1H, m), 5.11 (1H, dd, =1.4, 1.4), 5.04 (1H, ddd, J=6.6, 3.0, 1.5), 3.28 (1H, d, J=6.6); 13C NMR δ143.81, 137.13, 129.34, 125.59, 119.49, 116.95, 39.18; HRMS (EI) calcd for C9H10N2O2 178.0742, found 178.0746.

Provenance & Evidence