3-(4-BROMO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER

Chemical Properties

Clear yellow to light brown liquid

Uses

Ethyl 3-(4-bromophenyl)-3-oxo-propionate

Uses

Ethyl (4-bromobenzoyl)acetate may be used to synthesize 2-(carboethoxy)-3-(4′-bromo)phenylquinoxaline 1,4-dioxide.

General Description

Ethyl (4-bromobenzoyl)acetate can be prepared by employing the following reagents:

• ethyl acetylacetate
• petroleum ether
• NaOH
• 4-bromobenzoyl chloride

Synthesis

99-90-1

105-58-8

26510-95-2

Diethyl carbonate (295 g, 2.50 mol) was slowly added to a suspension of NaH (80 g, 60% mineral oil dispersion, 2 mol) in toluene (1.2 L) at 0 °C. After stirring at room temperature for 2 h, the mixture was slowly added dropwise under reflux conditions to a solution of p-bromoacetophenone (99 g, 0.50 mol) in toluene (400 mL). After the reaction mixture was refluxed overnight, it was cooled to room temperature and quenched sequentially with acetic acid (140 mL) and 2M aqueous hydrochloric acid (864 mL). The resulting mixture was extracted with ethyl acetate (400 mL x 3), the organic phases were combined, washed sequentially with water (500 mL x 4) and saturated saline (200 mL x 2) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was dried under vacuum to give ethyl (4-bromobenzoyl)acetate (122 g, 90% yield) as an oil.LC-MS (ESI): m/z 271.0 [M + H]+.

References

[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 31, p. 4543 - 4547
[2] Patent: WO2012/58125, 2012, A1. Location in patent: Page/Page column 147
[3] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1950 - 1956
[4] Archiv der Pharmazie, 2003, vol. 336, # 3, p. 181 - 190
[5] Molecules, 2004, vol. 9, # 3, p. 135 - 157