Benzyl chloroformate → benzyl N-(2-bromoethyl)carbamate

Participants

Reaction Steps

Twenty point five g (0.10 mole) of 2-bromoethylamine hydrobromide was dissolved in 140 ml of water. At 0° C., 15.3 g (0.089 mole) of benzylchloroformate was added, followed by 18.5 g (0.1 moles) of sodium bicarbonate, and the mixture was stirred for 15 minutes at 0°. The mixture was then stirred overnight at room temperature. The mixture was extracted with diethylether (3×250 ml), the combined portions of which were washed thrice with 150 ml portions of saturated sodium bicarbonate, dried with magnesium sulfate and evaporated to yield 20.98 g of the crude N-carbobenzyloxy-2-bromoethylamine (NCBA).

Provenance & Evidence