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

Participants

Reaction Conditions

Reaction Steps

To a solution prepared by adding 1,4-dioxane (50 mL) to benzyl chloroformate (17.5729 g; manufactured by Wako Pure Chemical Industries, Ltd.), an aqueous solution of 2-bromoethanamine hydrobromide-1,4-dioxane [104 mL; solution prepared by dissolving 2-bromoethanamine hydrobromide (21.3617 g; manufactured by Tokyo Chemical Industry Co., Ltd.) in water (54 mL) and 1,4-dioxane (54 mL)]and a 2 mol/L aqueous solution of sodium hydroxide (104 mL; manufactured by Kanto Chemical Co., Inc.) were simultaneously added dropwise. The mixture was stirred for 2 hours at 0° C. Water was added to the reaction solution, and the mixture was extracted two times with ethyl acetate. The organic layer was washed with a saturated solution of sodium hydrogen carbonate, and was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=94:6→73:27), and thus the title compound (19.2014 g) was obtained.

Provenance & Evidence