[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]([CH3:17])=[CH2:16])=[C:8]([Cl:18])[CH:7]=1.[OH-].[Na+]>ClCCl>[Br:5][C:6]1[CH:11]=[C:10]2[C:9](=[C:8]([Cl:18])[CH:7]=1)[O:12][CH2:13][CH2:14][C:15]2([CH3:17])[CH3:16]To a mixture of aluminum chloride (403 mg, 3.03 mmol) and dichloromethane (10.0 mL) cooled to −78° C. was added 4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)oxy]benzene (758 mg, 2.75 mmol) in dichloromethane (6.00 mL) via a cannula to give a light yellow solution. The reaction mixture was allowed to warm to room temperature, stirred for 5 minutes, and then poured into an Erlenmeyer flask containing a cold 10% NaOH solution (75.0 mL). The mixture was extracted with hexane (40.0 mL, 3×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% EtOAc/hexanes to afford the desired product as a colorless oil.
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