Réaction #3059

Équation de réaction

O-benzylhydroxylamine hydrochloride

bromoacetyl bromide

diisopropylethylamine

→

title compound

Rendement 52.0%

Bromo-N-(benzyloxyl)acetamide

Rendement 52.0%

Solvants

ethyl acetate

water

THF

Conditions de réaction

Traitement

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

Mode opératoire

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