Water → benzyl N-(2-bromoethyl)carbamate

Participants

Reaction Steps

Treat a 0° C. solution of 2-bromoethylamine hydrobromide (50 g, 0.246 mol) in dioxane (500 mL) with aqueous NaOH (1 M, 492 mL, 0.492 mol), add benzyl chloroformate (21.6 g, 0.127 mol) dropwise, warm to RT and stir overnight. Pour the mixture into H2O, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (60 g, 95%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.37-7.33 (m, 5H), 5.12 (s, 2H), 3.61 (t, J=5.6 Hz, 2H), 3.47 (t, J=5.6 Hz, 2H).

Provenance & Evidence