Allyl bromide → HCID 15549374, compound

Participants

Reaction Steps

A mixture of 5-cyano-2-nitro-phenol (3.0 g, 18.9 mmol), allyl bromide (1.82 ml, 21.0 mmol) and cesium carbonate (7.39 g, 22.7 mmol) in DMF (20 ml) was stirred at rt for 18 hrs under Ar. The reaction mixture was partitioned between t-butyl-methylether and water. The layers were separated and the aqueous portion was further extracted (×3). The combined organic extracts were washed twice with water, then brine and dried over MgSO4 and filtered. Removal of solvent at reduced pressure afforded the title compound (3.89 g, 100%). 1H NMR(400 MHz, CDCl3) δ 7.87 (d, J=8.5 Hz, 1H), 7.35 (dd, J=8.4 Hz J=1.2 Hz 1H), 7.35 (d, J=1.5 Hz, 1H), 6.02 (m, 1H), 5.52 (d, 1H), 5.43 (d, 1H), 4.73 (dd, J=3.6 Hz J=1.2 Hz 2H);

Provenance & Evidence