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

Participants

Reaction Conditions

Reaction Steps

To a 1,4-dioxane (50 mL) solution comprising benzylchloroformate (17.5729 g; manufactured by Wako Pure Chemical Industries, Ltd.), an aqueous solution of 2-bromoethane amine hydrogen bromide salt-1,4-dioxane [104 mL; solution which was prepared by dissolving 2-bromoethane amine hydrogen bromide salt (21.3617 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) in water (54 mL) and 1,4-dioxane (54 mL)] and an aqueous solution of 2 mol/L-sodium hydroxide (104 mL; manufactured by Kanto Chemical Co., Inc.) were added dropwise simultaneously, and stirred at 0° C. for 2 hours. The reaction solution was added with water and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with saturated sodium hydride, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=94:6→73:27) to obtain the title compound (19.2014 g).

Provenance & Evidence