1,2-Dibromoethane → Methyl 3-(2-bromoethoxy)benzoate

Temperature

85 °C

To a solution of methyl 3-hydroxybenzoate (2.00 g, 13.1 mmol) in acetone (50 ml) were added potassium carbonate (3.18 g, 230 mmol) and 1,2-dibromoethane (6.4 ml, 74.1 mmol) and the mixture was stirred at 85° C. for 24 hours. After cooling, the resultant was concentrated under reduced pressure. To the residue was added 75 ml of water and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution, water and saturated brine in this order, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1.79 g (6.9 mmol) of the titled compound as an yellow oil. Yield: 53%.

1. temperatureAfter cooling
2. concentrationthe resultant was concentrated under reduced pressure
3. additionTo the residue was added 75 ml of water
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with 1N aqueous sodium hydroxide solution, water and saturated brine in this order
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-0abbfe3f9bc54727a08ae8f4cb7c7982

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012964B2