Water → benzyl N-(2-bromoethyl)carbamate

Temperature

0 °C

To a solution of 2-bromoethylamine hydrobromide (120.0 g) in chloroform (1400 ml) was added triethylamine (204 ml), and thereto was added dropwise benzyl chloroformate (100 ml) under ice-cooling slowly. The mixture was stirred at 0° C. for one hour, and warmed to room temperature, and further stirred overnight. To the reaction mixture was added water, and the mixture was extracted twice with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and dried under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to give the title compound (110 g).

1. temperaturecooling slowly
2. temperaturewarmed to room temperature
3. stirringfurther stirred overnight
4. extractionthe mixture was extracted twice with chloroform
5. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customdried under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1)

ORD record

ord-4518cf0359ed43a08fd61d6496026984

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658639B2