Reaction #3059

Reaction equation

O-benzylhydroxylamine hydrochloride

bromoacetyl bromide

diisopropylethylamine

→

title compound

Yield 52.0%

Bromo-N-(benzyloxyl)acetamide

Yield 52.0%

Solvents

ethyl acetate

water

THF

Conditions

Workup

1. 1
   OtherThe aqueous layer was separated
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane

Procedure

To a 0° C. solution of O-benzylhydroxylamine hydrochloride (1.6 g, 10 mmol) in THF (40 mL) was added bromoacetyl bromide (871 μL, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol). The reaction mixture was warmed to room temperature overnight and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane to give 1.27 g (52%) of the title compound.

Source