Bromoacetyl bromide → HCID 13944533, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-benzyl-2-oxazolidinone in dry THF (300 ml) was stirred at −78° C. under nitrogen during the dropwise addition of 1.6 M n-butyl lithium in hexanes, (60 ml, 97 mmol) followed by bromo-acetyl bromide. The pale yellow solution was stirred for a further 10 minutes at −78° C. and allowed to warm to room temperature over 30 minutes. The reaction was then quenched by the addition of saturated aqueous ammonium chloride solution. After dilution with ethyl acetate and brine, the two layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 4-benzyl-3-(2-bromo-acetyl)-oxazolidin-2-one (26.2 g) which was used in the next step without further purification.

Provenance & Evidence