Ethylene Glycol → 2-Hydroxyethyl 2-Bromopropionate

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%):

1. customto separate into two layers
2. washThe organic layer is washed with dilute hydrochloric acid and brine
3. dry with materialdried over Na2SO4
4. distillationthe volatile matter is then distilled off under reduced pressure
5. customto give a crude product (3.07 g)
6. distillationThis crude product is distilled under reduced pressure (70˜73, 0.5 mmHg)

ORD record

ord-2102053da2434c6b822ec5fc63385942

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274688B1