Ethyl bromoacetate → Ethyl (2-hydroxy-4-nitrophenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

4-Nitrocatechol (5 g, 32.2 mmol) was dissolved in DMF (50 ml); thereafter, potassium carbonate (8.9 g, 64.5 mmol) was added and with heating at 70-75° C., ethyl bromoacetate (7.18 ml) was slowly added dropwise, followed by stirring at the same temperature for 15 min. The reaction solution was cooled to room temperature and filtered; after being concentrated under vacuum, the filtrate was diluted with a saturated aqueous solution of sodium bicarbonate (50 ml) and subjected to extraction with ethyl acetate (300 ml). The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated. The resulting residue was purified by being subjected to column chromatography on silica gel using a 2:1 solvent system of n-hexane and ethyl acetate as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound ethyl (2-hydroxy-4-nitrophenoxy)acetate (1.05 g).

Provenance & Evidence