Ethylene Glycol → 2-Hydroxyethyl 2-Bromopropionate

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%).

1. customto separate into two layers
2. customThe organic layer was separated
3. washwashed with diluted hydrochloric acid and brine
4. dry with materialdried over sodium sulfate
5. distillationthe volatile matter was distilled off under reduced pressure
6. customto give a crude product (3.07 g)
7. distillationDistillation of this crude product under reduced pressure (70-73° C., 0.5 mmHg)

ORD record

ord-c35ad81618214451949321f9a0e881a8

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06194516B1