[C:1]([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[CH:7]=1)(=[O:3])[CH3:2].CC(O)=O.[Br:16]N1C(=O)CCC1=O.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>>[C:1]([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[C:7]=1[Br:16])(=[O:3])[CH3:2]To a solution of (3-methylisoxazol-5-yl)methyl acetate (0.979 g, 6.31 mmol) in AcOH (10 mL, 175 mmol) was added N-bromosuccinimide (1.30 g, 7.30 mmol) and H2SO4 (0.65 mL, 12.19 mmol). The reaction was heated to 110° C. After 1 h, the reaction mixture was cooled to room temperature and carefully poured into a beaker containing ice and saturated NaHCO3. The bi-phasic was vigorously stirred and basic solution (pH ˜8-9) was extracted with EtOAc (2×15 mL). The organic layer was washed with 2% sodium thiosulfate, washed with brine (20 mL), dried over Na2SO4, and concentrated to give a light yellow oil. The oil was purified on Biotage system (isocratic elution 10% EtOAc:90% Hexanes) to give the titled compound (1.30 g, 5.55 mmol, 88% Yield) as a colorless yellow oil. LC/MS m/z 234 [M+H]+.
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