Ethyl bromoacetate → Ethyl 2-(3-bromophenoxy)acetate

3-Bromophenol (2.84 g, 16.4 mmol) was dissolved in dimethylformamide (50 ml) in a dry 100 ml flask under nitrogen. Sodium hydride (0.7 g of a 60% suspension in mineral oil, washed with hexane, 16.7 mmol) was added in portions and the mixture was stirred for one hour at room temperature. Ethyl bromoacetate (1.85 ml, 16.7 mmol) was added drop-wise and the reaction was stirred overnight at room temperature. Approximately two-thirds of the solvent was removed under reduced pressure and the residue was mixed with water (150 ml) and extracted with methylene chloride (3×20 ml). The extracts were combined, washed with water (50 ml), saturated sodium chloride solution (50 ml), then dried (MgSO4). The solution was filtered and concentrated which gave 4.18 g (98%) of ethyl 3-bromophenyloxyacetate.

1. washSodium hydride (0.7 g of a 60% suspension in mineral oil, washed with hexane, 16.7 mmol)
2. additionwas added in portions
3. stirringthe reaction was stirred overnight at room temperature
4. customApproximately two-thirds of the solvent was removed under reduced pressure
5. additionthe residue was mixed with water (150 ml)
6. extractionextracted with methylene chloride (3×20 ml)
7. washwashed with water (50 ml), saturated sodium chloride solution (50 ml)
8. dry with materialdried (MgSO4)
9. filtrationThe solution was filtered
10. concentrationconcentrated which

ORD record

ord-97f1d9d1aa564e47b02edbd5a04157c9

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05444050