Chemical Properties
Ethyl 3-bromo-2-oxobutyrate is Clear Colourless Oil
Uses
Ethyl α-Bromoethylglyoxalate is used in the preparations of potential positron emission tomography tracers for neuropeptide Y Y1 receptors.
Uses
Ethyl 3-bromo-2-oxobutyrate is used in the preparations of potential positron emission tomography tracers for neuropeptide Y Y1 receptors.
Synthesis Reference(s)
The Journal of Organic Chemistry, 67, p. 1102, 2002
DOI: 10.1021/jo010630z
Synthesis
Step A: Synthesis of ethyl 3-bromo-2-oxobutanoate (1-B). Bromine (1.89 mL, 36.9 mmol) was added slowly and dropwise to a solution of ethyl 2-oxobutyrate (1-A, 4.8 g, 36.9 mmol) in dichloromethane (20 mL) at 5 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 18 hours. Upon completion of the reaction, the reaction mixture was purged with nitrogen to remove residual bromine. Subsequently, the reaction mixture was diluted with ethyl acetate and the organic phase was washed sequentially with 10% sodium bicarbonate solution (2 times), water and saturated saline. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give ethyl 3-bromo-2-oxobutanoate as a yellow oil (1-B, 7.50 g, 97% yield).1H-NMR (CDCl3) data: δ 5.15-5.20 (q, 1H), 4.32-4.45 (m, 2H), 1.82-1.85 (d, 3H), 1.38- 1.41 (t, 3H).
References
[1] Patent: US2012/149699, 2012, A1. Location in patent: Page/Page column 14-15
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1823 - 1838
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1116 - 1139
[4] Patent: WO2016/4105, 2016, A1. Location in patent: Paragraph 00146
[5] Tetrahedron, 2013, vol. 69, # 2, p. 474 - 480
