Ethylene Glycol → 2-Hydroxyethyl 2-Bromopropionate

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Reaction Steps

In a nitrogen atmosphere, 2-bromopropionyl chloride (2 mL, 3.35 g, 19.5 mmol) was slowly added dropwise to a solution of ethylene glycol (10.9 mL, 195 mmol) and pyridine (3 g, 39 mmol) in THF (10 mL) at 0° C. The resulting solution was then stirred at that temperature for 2 hours. Diluted hydrochloric acid (20 mL) and ethyl acetate (30 mL) were added and the mixture was allowed to separate into two layers. The organic layer was separated, washed with diluted hydrochloric acid and brine and dried over sodium sulfate, and the volatile matter was distilled off under reduced pressure, to give a crude product (3.07 g). Distillation of this crude product under reduced pressure (70°-73° C., 0.5 mmHg) gave 2-hydoxyethyl 2-bromopropionate of the formula shown below (2.14 g, 56%).

Provenance & Evidence