F[B-](F)(F)F.[H+].Br[CH:8]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9]1.C([O-])(O)=[O:17].[Na+].[OH-].[K+]>O1CCOCC1.[Hg]=O>[C:8]1([OH:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=1To a stirred solution of mercury(II) oxide (591.3 mg, 2.73 mmol) and 35% aqueous tetrafluoroboric acid (TFBA) (999.4 mg, 5.46 mmol) in 1,4-dioxane (10.9 mL), 1-bromobenzocyclobutene (1.0 g, 5.46 mmol) was added. The reaction stirred at room temperature for 2 h and was then treated successively with NaHCO3 and 3N KOH until the solution remained basic. The precipitated mercury(II) oxide was filtered off and the filtrate extracted with CH2Cl2 (3×300 mL), dried with anhydrous Na2SO4, filtered, and concentrated to yield white crystals that were purified via column chromatography using a 3:2 Hexanes:EtOAc solvent system.
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