Sodium Carbonate → 2-Methoxy-6-(4-methoxyphenyl)naphthalene

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Reaction Steps

In an 100 mL three-necked RB flask equipped with a magnetic bar, a condenser and a nitrogen gas inlet, 2-bromo-6-methoxynaphthalene (7.32 g, 30 mmol), 4-methoxybenzene boronic acid (4.86 g, 32 mmol) and 1-propanol (50 mL) were mixed and stirred at room temperature for approx. 30 min. Palladium acetate (0.02 g, 0.09 mmol), triphenylphosphine (0.07 g, 0.27 mmol), Na2CO3 solution (2M, 18 mL, 36 mmol) and water (10 mL) were added and the mixture was refluxed for 1.5 h. When the mixture was still hot, 30 mL of water was added and the mixture was stirred and cooled to room temperature. The resultant crystals were filtered, washed with water and recrystallized from acetone to give the DMPN title compound as colorless flakes (6.86 g, 86%). mp 194-196° C. (DSC 196° C.). 1H NMR (500 MHz, CDCl3) δ 3.88 (s, 3H), 3.95 (s, 3H), 7-8 (m, 10H). IR (KBr) ν (cm−1): 3058 (Ph—H, w), 1028 (OCH3, s). Anal. Calcd for C18H16O2: C, 81.79; H, 6.10. Found: C, 81.80; H, 6.25. GC-MS (m/z) 264 (M+).

Provenance & Evidence