[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>CC#N.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>[Br:14][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]The above compounds were prepared according to the procedure reported in the literature: see D. Yang, J. Org. Chem. 2002, 67, 7429. MS: 258, 260 (M+1). To a solution of ethyl 2-(pyridin-4-yl)propanoate (5.3 g, 30 mmol), Mg(ClO4)2 (Aldrich, 2.0 g, 9.0 mmol) in CH3CN (60 mL) was added N-bromosuccinimide (Aldrich, 5.9 g, 33 mmol) at room temperature. After 2 h, the reaction mixture was diluted with ether (200 mL), and 10% Na2CO3. The organic phase was separated, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. Mass Spec. m/z+ion 258, 260 (M+1).
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