Sodium Carbonate → 3-Methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenylnaphthalene

Participants

Reaction Conditions

Reaction Steps

2-Bromo-3-methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}naphthalene (14) (2.32 g, 7.46 mmol), phenylboronic acid (1.83 g, 15.0 mmol, 2.0 eq), tetrakistriphenylphosphine palladium (0) (0.869 g, 0.752 mmol, 10 mol %), 2 M sodium carbonate (65 mL), and ethylene glycol dimethyl ether (65 mL) were combined in a glass pressure bottle. The bottle was sealed with a screw cap and the reaction mixture was heated at 160° C. with stirring for 25 min. The reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and extracted with Et2O. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated to give 4.96 g of the crude product. The crude product was combined with an additional 4.43 g of crude product (from a second Suzuki coupling reaction) and purified the crude product by chromatography over SiO2 with hexanes:CH2Cl2 (2:3) to give 4.2 g (91%) of the title compound (15) as a yellow oil. 1H NMR (400 MHz; DMSO-d6): δ 2.13 (s, 3H), 2.98 (s, 3H), 3.86 (s, 3H), 4.64 (s, 2H), 7.13 (dd, J=2.4 Hz, 9.1 Hz, 1H), 7.25 (d, J=2.4 Hz, 1H), 7.29 (d, J=7.0 Hz, 2H), 7.36 (t, J=7.5 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.51 (s, 1H), 7.94 (d, J=9.1 Hz, 1H).

Provenance & Evidence