[OH-:1].[Na+].BrBr.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])C)=[C:11]([Br:18])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>O.O1CCOCC1>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:1])=[C:11]([Br:18])[CH:10]=1)([CH3:6])([CH3:7])[CH3:8]A solution of NaOH (7.8 g, 190 mmol) in water (60 mL) was cooled in an ice bath, and bromine (2.51 mL, 49 mmol) was slowly added. A solution of 1-(4-tert-butyl-2-bromophenyl)ethanone (3.1 g, 12 mmol) in dioxane (60 mL) was slowly added, and the cooling bath was removed. After being stirred at room temperature for 3 h the reaction was acidified with concentrated hydrochloric acid. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4, and concentrated under vacuum to give 4-tert-butyl-2-bromobenzoic acid (3.1 g, 100% yield) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=8.3 Hz, 1H), 7.71 (d, J=1.9 Hz, 1H), 7.41 (dd, J=8.3, 1.9 Hz, 1H), 1.34 (s, 9H) ppm.
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