Ethyl 3-bromo-2-oxobutyrate synthesis
- Product Name:Ethyl 3-bromo-2-oxobutyrate
- CAS Number:57332-84-0
- Molecular formula:C6H9BrO3
- Molecular Weight:209.04
15933-07-0
57332-84-0
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).
15933-07-0
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57332-84-0
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Yield:57332-84-0 97%
Reaction Conditions:
with bromine in dichloromethane at 5 - 20;
Steps:
1.A
Step A: Ethyl 3-bromo-2-oxobutanoate (1-B). To a solution of compound 1-A (4.8 g, 36.9 mmol) in CH2Cl2 (20 mL), cooled to 5° C., was added bromine (1.89 mL, 36.9 mmol), drop-wise. The reaction mixture was allowed to warm to room temperature and stir for 18 h. The reaction mixture was purged with nitrogen, diluted with EtOAc, and the organic phase washed with 10% NaHCO3 (2*), H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure to afford compound 1-B as a yellow oil (7.50 g, 97%). 1H-NMR (CDCl3): 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:
Macielag, Mark J.;Xia, Mingde;McNally, James J.;Matthews, Jay M. US2012/149699, 2012, A1 Location in patent:Page/Page column 14-15
52089-54-0
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57332-84-0
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57332-84-0
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