2-Bromo-6-methoxynaphthalene → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0) (120 mg) and cuprous bromide (20 mg) were added to a solution of 2-bromo-6-methoxynaphthalene (0.3 g, 1.27 mmol) and trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane, 62, (0.45 g, 1.37 mmol) in THF (30 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 for 16 h. After cooling, THF was evaporated and 50 mL ethyl acetate was added to the residue. The solution was washed with water. The organic layer was separated and passed through a Celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4), and evaporated in vacuo. The residue was chromatographed using a 80:20 mixture of hexanes:ethyl acetate to give the desired product 45 (0.29 g) in 71% yield; mp 165-167° C.; IR (KBr) 2911, 1609, 1520, 1482, 1429, 1393, 1344, 1257, 1199 cm−1; 1H NMR (CDCl3) δ3.94 (3H, s), 6.14 (2H, s), 6.88 (1H, s), 7.16-7.21 (2H, m), 7.31 (1H, dd, J1=8.5, J2=1.9), 7.47 (1H, s), 7.67-7.77 (3H, m); 13C NMR δ55.89, 103.45, 105.92, 106.19, 111.69, 119.86, 126.90, 127.02, 127.55, 129.23, 130.09, 133.76, 133.85, 134.48, 143.38, 147.52, 151.47, 158.62; HRMS (EI) calcd for C18H13NO5 m/z: 323.0794; found: 323.0788.

Provenance & Evidence