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) is added dropwise slowly at 0° C. to a THF (tetrahydrofuran) solution (10 mL) of ethylene glycol (10.9 mL, 195 mmol) and pyridine (3 g, 39 mmol). The solution is stirred at that temperature for 2 hours. Dilute hydrochloric acid (20 mL) and ethyl acetate (30 mL) are added and the mixture is allowed to separate into two layers. The organic layer is washed with dilute hydrochloric acid and brine and dried over Na2SO4, and the volatile matter is then distilled off under reduced pressure to give a crude product (3.07 g). This crude product is distilled under reduced pressure (70˜73, 0.5 mmHg) to give hydroxyethyl 2-bromopropionate of the formula shown below (2.14 g, 56%):

Provenance & Evidence