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

Temperature

0 °C

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 (1.3 mmHg), 2.986 g) of the formula shown below.

1. customA 50-mL two-necked flask is purged with nitrogen
2. filtrationthe resulting pyridine hydrochloride is filtered off
3. washThe filtrate is washed with dilute hydrochloric acid (10 mL)
4. dry with materialThe organic layer is dried over Na2SO4
5. distillationthe volatile matter is distilled off under reduced pressure
6. customThe crude product thus obtained
7. distillationis distilled under reduced pressure

ORD record

ord-45e04bb14f6445899e0317f4975b7659

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274688B1