N,N-Dimethylaniline → 2-Methylpropyl 2-bromoacetate

Participants

Reaction Steps

Over a period of 6-8 hours there was added dropwise 1 M of bromoacetyl bromide to a stirred solution of 1 M of isobutyl alcohol, 1 M of dimethylaniline and 200 ml of anhydrous ether. The solution was kept just below boiling by adjusting the rate of addition and by occasional cooling in an ice bath. After complete addition, the mixture was stirred overnight at room temperature. Water (100 ml) was added and the mixture stirred until all of the precipitate had dissolved. The layers were separated and the ether layer was washed with 100 ml portions of 10% sulfuric acid until neutralization of the washings resulted in a clear solution. The washed ether solution was dried over anhydrous sodium sulfate and after removal of the drying agent and solvent the residue was distilled in vacuo. The recovered product had a bp / 14 mm = 72° - 76° C, n25 = 1.4468.

Provenance & Evidence