1-Propanol → 2-Ethoxy-1-nitro-4-vinylbenzene

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-2-nitrophenyl ethyl ether (8.8 g, 35.76 mmol) in 80 mL of n-propanol was added, PdCl2(dppf)*DCM (0.523 g, 0.72 mmol), potassium ethenyl(trifluoro)borate (6.71 g, 50 mmol), and TEA (3.61 g, 35.76 mmol). The mixture was heated to 100° C. for 3 h. The solvent was rotovaped down and the residue dissolved in DCM, and filtered to remove insoluble solids. 20 g of silica gel was added and the solvent rotovaped down, and purified by flash chromatography to give the title compound of step B (5.58 g, 28.89 mmol, 81%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (d, J=8.97 Hz, 1H), 7.01-7.03 (m, 1H), 6.68 (dd, J=17.67, 10.71 Hz, 1H), 5.84 (d, J=17.58 Hz, 1H), 5.44 (d, J=11.17 Hz, 1H), 4.19 (q, J=6.96 Hz, 2H), 1.47 (t, J=6.96 Hz, 3H).

Provenance & Evidence