| Identification | Back Directory | [Name]
3-BROMO-2-OXOPENTANEDIOIC ACID DIMETHYL ESTER | [CAS]
148728-48-7 | [Synonyms]
Dimethyl 3-bromo-2-oxoglutarate
DiMethyl 3-broMo-2-oxopentanedioate
3-BROMO-2-OXOPENTANEDIOIC ACID DIMETHYL ESTER
Pentanedioic acid, 3-bromo-2-oxo-, dimethyl ester
beta-Bromo-alpha-ketoglutaric acid dimethyl ester
Pentanedioic acid, 3-bromo-2-oxo-, 1,5-dimethyl ester | [Molecular Formula]
C7H9BrO5 | [MDL Number]
MFCD20526357 | [MOL File]
148728-48-7.mol | [Molecular Weight]
253.05 |
| Hazard Information | Back Directory | [Uses]
Dimethyl 3-?Bromo-?2-?oxopentanedioate is an intermediate in synthesizing Dimethyl 2-Oxoglutaconate (D476450), a useful synthetic intermediate. | [Synthesis]
Step A: Synthesis of dimethyl 3-bromo-2-oxoglutarate
To a solution of EtOAc (160 mL) in CuBr2 (11.5 g, 51.7 mmol) was added a CHCl3 solution (80 mL) of dimethyl 2-oxoglutarate (3.00 g, 17.2 mmol). The reaction mixture was refluxed overnight and cooled to room temperature. The volatile solvent was evaporated and the residue was purified by SiO2 column chromatography (eluent: hexane/ethyl acetate = 3:2) to afford dimethyl 3-bromo-2-oxoglutarate (4.36 g, quantitatively) as a yellow oil.
1H NMR (CDCl3, Varian 400 MHz): δ 3.06 (1H, ABX, Jab = 17.3 Hz, Jax = 9.3 Hz), 3.34 (1H, ABX, Jab = 17.3 Hz, Jbx = 5.9 Hz), 3.71 (3H, s), 3.95 (3H, s), 5.40 (1H, ABX, Jax = 9.3 Hz). Jax = 9.3 Hz, Jbx = 5.9 Hz). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[2] Patent: US2012/238599, 2012, A1. Location in patent: Page/Page column 32
[3] Journal of Organic Chemistry, 2002, vol. 67, # 4, p. 1102 - 1108
[4] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 2, p. 176 - 180
[5] Journal of the American Chemical Society, 1981, vol. 103, p. 5599 |
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