Allylamine → Allyl-(3-fluoro-6-nitro-2-vinylphenyl)amine

Participants

Reaction Steps

To a solution of 1,3-difluoro-4-nitro-2-vinylbenzene (115 mg, 0.621 mmol) in DMF (3 mL) was added allylamine (0.0513 mL, 0.683 mmol) and potassium carbonate (0.173 g, 1.24 mmol). The reaction mixture was stirred at RT for 2 h, and then partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 1-5% EtOAc in cyclohexane) affording the title compound as a yellow oil (109.6 mg, 79%). 1H NMR (CDCl3, 300 MHz): 8.08 (1H, dd J=9.4, 5.8 Hz), 7.64 (1H, bs), 6.57 (1H, t, J=9.3 Hz), 6.51 (1H, dd, J=18.0, 11.6 Hz), 5.81 (1H, tdd, J=17.1, 10.2, 5.5 Hz), 5.72 (1H, ddd, J=18.0, 2.5, 1.6 Hz), 5.65 (1H, ddd, J=11.6, 1.5, 0.9 Hz), 5.26 (1H, dq, J=17.1, 1.5 Hz), 5.17 (1H, dq, J=10.2, 1.4 Hz), 3.98 (2H, ddt, J=6.3, 5.5, 1.6 Hz)

Provenance & Evidence