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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-hydroxybenzoate (2.00 g, 13.1 mmol) in acetone (50 ml) were added potassium carbonate (3.18 g, 23.0 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%.

Provenance & Evidence