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

Temperature

0 °C

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.

1. customTo a solution prepared
2. customsolution prepared
3. additionwere simultaneously added dropwise
4. extractionthe mixture was extracted two times with ethyl acetate
5. washThe organic layer was washed with a saturated solution of sodium hydrogen carbonate
6. dry with materialwas dried over magnesium sulfate
7. concentrationThe organic layer was concentrated under reduced pressure
8. customThe resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=94:6→73:27)

ORD record

ord-52fcf76da7dc45ffbc35eb0cb2ef4374

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008506B2