Water → 2-bromo-N,N-diethylacetamide

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a 1-liter flask is charged with 2-bromoacetylbromide (46.34 g, 230 mmol) and 300 ml ether. The flask is chilled to −15° C., and a solution of diethylamine (33.72 g, 460 mmol) in 200 ml ether is added over 1 hour to the flask. The resulting thick slurry is stirred cold for 1 additional hour, then warmed slowly to room temperature, and stirred overnight. The mixture is added to 250 ml cold water, and the resulting aqueous solution is extracted with ether (3 times, 200 ml ether each time). The combined ether extracts are washed with phosphoric acid (5 wt percent, 200 ml), aqueous potassium carbonate (8 wt percent, 200 ml) and thereafter brine (150 ml). The ether extract is then dried over sodium sulfate and concentrated in vacuo to a light brown residue. The residue is vacuum distilled to yield 2-bromo-N,N-diethylacetamide as a clear, colorless oil (22.99 g, 52% yield). 1H NMR (300 MHz, CDCl3), δ (PPM): 1.08 (t, 3H), 1.20 (t, 3H), 3.33 (q, 4H), 3.79 (s, 2H).

Provenance & Evidence