Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](C)C)[C:3]=1OC.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+].[CH2:32]([O:34][CH2:35][CH3:36])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC.O>[CH:4]([C:3]1[CH:2]=[CH:7][CH:6]=[C:36]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:35]=1[O:34][CH3:32])([CH3:8])[CH3:5]In a flask charged with 2-bromo-6-isopropylanisole (1.98 g, 8.64 mmol), phenylboronic acid (2.10 g, 17.28 mmol), palladium acetate (96 mg, 0.43 mmol), triphenylphosphine (0.225 g, 0.86 mmol) and potassium phosphate (11 g, 51.84 mmol), mixture of water (8 mL) and dimethoxyethane (32 mL) was added, and the resultant mixture was heated under reflux for 12 hours. After cooling to ambient temperature, aqueous ammonium chloride (15 mL) and diethyl ether (30 mL) were charged thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. Combined organic layer was dried over magnesium sulfate, and evaporated to remove the volatiles to obtain 2-isopropyl-6-phenylanisole as grey solid (2 g). The anisole obtained (without further purification) was dissolved in methylene chloride (15 mL), and 12 mL of boron tribromide solution (1 M in methylene chloride) was added dropwise thereto at −78° C. Reaction was carried out for 12 hours while slowly raising the temperature to ambient temperature. When the reaction was completed, mixture of water (15 mL) and diethyl ether (30 mL) was added thereto. After isolating the organic layer, the aqueous layer was extracted with diethyl ether (15 mL×3). The combined organic layer was dried, and evaporated under reduced pressure to remove the volatiles. The residue was purified via silica gel column by using mixed solvent of hexane and methylene chloride to obtain 2-isopropyl-6-phenylphenol (1.72 g) as white solid.
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