Sodium Hydroxide → 1-(2,6-Dimethoxyphenyl)naphthalene

Participants

Reaction Steps

To a solution of 1-bromo-2,6-dimethoxybenzene, (2.63 g, 12.1 mmol), tetrakis(triphenylphosphine)palladium (0) (0.91 g, 0.76 mol) and 1-naphthylboric acid (4.16 g, 23.9 mmol) in 1,4-dioxane (160 ml), a 2N aqueous solution of sodium hydroxide (13 ml) was added, and the mixture was heated to reflux. After cooling, the solvent was evaporated off, and the residue was dissolved in diethyl ether. The diethyl ether solution was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated off, and the residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1) to obtain 1-naphthyl-2,6-dimethoxybenzene (2.50 g).

Provenance & Evidence