[H+].[B-](F)(F)(F)F.CCOCC.[CH3:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[Br:25]N1C(=O)CCC1=O.OS([O-])(=O)=O.[Na+]>C(#N)C>[CH3:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([Br:25])[CH:18]=1Add HBF4-Et2O (4.4 mL, 27.7 mmol) to methyl-3-(4-hydroxyphenyl)-propionate (5.0 g, 27.7 mmol) in acetonitrile with stirring at 0° C. After 10 minutes, add N-bromosuccinimide (5.4 g, 30.5 mmol) and gradually allow to warm to room temperature. After 18 hours, pour into 38% NaHSO4 and extract with diethyl ether. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to provide the title compound.
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