o-Iodonitrobenzene → 6-(2-Nitrophenyl)-2,3-dimethoxy-7,8-dihydronaphthalene

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (840 mg, 1.2 mmol) and sodium acetate (200 mg, 2.4 mmol) were added to a solution of 6,7-dimethoxy-3,4-dihydronaphthalene (2, 700 mg, 3.7 mmol) and 1-iodo-2-nitrobenzene (925 mg, 3.7 mmol) in dimethylacetamide (50 mL). The mixture was stirred under nitrogen at 140° C. overnight, and then concentrated in vacuo. Ethyl acetate (60 mL) was added to the residue and washed with distilled water (50 mL). The organic layer was separated and passed through a celite bed. The organic layer was then washed with brine, dried (anhydrous Na2SO4) and concentrated in vacuo. The residue was chromatographed to give compound 3 (330 mg) in 29% yield; 1H NMR (CDCl3) d 2.51(2H, t, J=8.1), 2.92(2H, t, J=8.1), 3.87(3H, s), 3.90(3H, s), 6.45(1H, s), 6.67(1H, s), 6.73(1H, s), 7.38˜7.45 (2H, m), 7.54˜7.62(1H, m), 7.88˜7.93(1H, m); 13C NMR d 28.5, 28.5, 56.6, 111.0, 111.7, 124.9, 127.0, 127.1, 128.1, 128:3, 131.3, 133.3, 135.7, 138.7, 147.9, 148.9.

Provenance & Evidence