Pyridine → 2-[(Prop-2-en-1-yl)oxy]ethyl 2-bromopropanoate

Participants

Reaction Conditions

Reaction Steps

A 50-mL two-necked flask is purged with nitrogen and then charged with 2-allyloxyethanol (2.5 mL, 23.4 mmol), pyridine (3 mL) and THF (10 mL). The solution is cooled to 0° C., and 2-bromopropionyl chloride (2 mL, 19.52 mmol) is added dropwise slowly. The resulting mixture is stirred at that temperature for an hour, then ethyl acetate (10 mL) is added, and the resulting pyridine hydrochloride is filtered off. The filtrate is washed with dilute hydrochloric acid (10 mL), then with an aqueous solution of NaHCO3 (10 mL) and further with brine (10 mL). The organic layer is dried over Na2SO4 and the volatile matter is distilled off under reduced pressure. The crude product thus obtained is distilled under reduced pressure to give allyloxyethyl 2-bromopropionate (78.5–81° C. (1.3 mmHg), 2.986 g) of the formula shown below. CH3C(H)(Br)C(O)O—CH2CH2—O—CH2CH═CH2

Provenance & Evidence