[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]([C:13]([O:15]CC)=[O:14])[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>OC(C)=O.O.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([C:8]([OH:10])=[O:9])[C:13]([OH:15])=[O:14])=[CH:18][CH:19]=1Diethyl 2-(4-bromobenzyl)malonate (40 g, 13 mmol) and KOH (42.8 g, 76 mmol) was dissolved in a mixture of HOAc-H2O-THF (1:2:3, 200 mL), the mixture was refluxed for 12 hours. The solvent was removed in vacuo, the residue was added HCl aqueous, then extracted with EtOAc, washed with brine, dried over Na2SO4, concentrated to give 2-(4-bromobenzyl)malonic acid (31 g, 95%).
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