Ethyl bromoacetate → HCID 10264196, compound

Sodium hydride (min. 60% parafflnic dispersion, 2.95 g, about 74 mmol) was washed with anhydrous hexane in a nitrogen stream and suspended in anhydrous dimethylformamide. The obtained suspension was stirred under cooling with ice, followed by the dropwise addition of a solution of ethyl 4-hydroxybenzoate (11.2 g, 67 mmol) in dimethylformamide. The obtained mixture was stirred at room temperature for 80 minutes and cooled with ice again, followed by the dropwise addition of a solution of ethyl bromoacetate (12.9 g, 77 mmol) in anhydrous dimethylformamide. The obtained mixture was stirred at room temperature to complete a reaction. The reaction mixture was filtered to remove insolubles and the filtrate was concentrated under a reduced pressure. The residue was dissolved in diethyl ether and the obtained solution was washed with an aqueous solution of sodium hydrogencarbonate and an aqueous solution of common salt, dried and distilled to remove the solvent. The residue was purified by silica gel column chromatography. Yield: 16.8 g.

1. temperatureunder cooling with ice
2. stirringThe obtained mixture was stirred at room temperature for 80 minutes
3. temperaturecooled with ice again
4. stirringThe obtained mixture was stirred at room temperature
5. customa reaction
6. filtrationThe reaction mixture was filtered
7. customto remove insolubles
8. concentrationthe filtrate was concentrated under a reduced pressure
9. dissolutionThe residue was dissolved in diethyl ether
10. washthe obtained solution was washed with an aqueous solution of sodium hydrogencarbonate
11. customan aqueous solution of common salt, dried
12. distillationdistilled
13. customto remove the solvent
14. customThe residue was purified by silica gel column chromatography

ORD record

ord-8d4e0e97d0404acf8d9cfc6b8633c905

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688800