[OH-].[Li+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]([O:21]C)=[O:20])=[CH:12][C:13]([N:16]([CH3:18])[CH3:17])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1>C1COCC1.CO.Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:19]([OH:21])=[O:20])=[CH:12][C:13]([N:16]([CH3:17])[CH3:18])=[CH:14][CH:15]=2)=[CH:8][CH:9]=12M Lithium hydroxide (8.5 mL, 17.0 mmol) was added to a solution of methyl 4′-bromo-4-(dimethylamino)biphenyl-2-carboxylate (1.9 g, 5.69 mmol) in THF (20 mL) and methanol (20 mL) and stirred at r.t. for 18 hrs. The reaction was then diluted with 1M HCl and extracted with EtOAc. The organic layer was washed with water then brine, dried over MgSO4, filtered and then evaporated to give 4′-bromo-4-(dimethylamino)biphenyl-2-carboxylic acid (1.34 g, 4.19 mmol, 74% yield) as a white solid. LCMS: rt=1.54 min. [M+H]+=319 and 321; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent. A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.
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