Triphenylphosphine → 1-[(2-Bromo-5-methoxybenzyl)oxy]-6-methoxynaphthalene

Participants

Reaction Steps

To a solution of 6-methoxynaphthol (12.9 g, 74.1 mmol), 5-methoxy-2-bromobenzyl alcohol (17.7 g, 81.6 mmol), and triphenylphosphine (31.1 g, 119 mmol) in THF (400 mL) was slowly added a solution of DEAD (20.6 g, 119 mmol) in THF (50 mL). The solution was stirred overnight, concentrated onto silica, and purified by silica column (10% ethyl acetate—hexanes) to yield 16.38 g (59%) of the title compound as a white solid: mp 83-84° C.; 1H NMR (CDCl3): δ 3.78 (3H, s), 3.92 (3H, s), 5.25 (2H, s), 6.75-6.77 (2H, m), 7.12 (1H, d, J=2.44 Hz), 7.15 (1H, dd, J=2.44 Hz, J=9.28 Hz), 7.24 (1H, d, J=2.93 Hz), 7.32-7.36 (2H, m), 7.48 (1H, d, J=8.79 Hz), 8.27 (1H, d, J=9.23 Hz); MS (ESI) m/z373/375 ([M+H]+);

Provenance & Evidence